dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-56b1f4bfeebc4b8ab990b9804e798aa7 | CC(C)N1CCNCC1.CCOC(=O)c1cnc2cc(OCC)c(Br)cc2c1Nc1ccc(F)cc1F>>CCOC(=O)c1cnc2cc(OCC)c(N3CCN(C(C)C)CC3)cc2c1Nc1ccc(F)cc1F | CCOC1=C(C=C2C(=C1)N=CC(=C2NC3=C(C=C(C=C3)F)F)C(=O)OCC)Br.CC(C)N1CCNCC1>>CCOC1=C(C=C2C(=C1)N=CC(=C2NC3=C(C=C(C=C3)F)F)C(=O)OCC)N4CCN(CC4)C(C)C | [NH:16]1[CH2:17][CH2:18][N:19]([CH:20]([CH3:21])[CH3:22])[CH2:23][CH2:24]1.Br[c:15]1[c:11]([O:12][CH2:13][CH3:14])[cH:10][c:9]2[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:27]([NH:28][c:29]3[cH:30][cH:31][c:32]([F:33])[cH:34][c:35]3[F:36])[c:26]2[cH:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]2[... | CC(C)N1CCNCC1.CCOC(=O)c1cnc2cc(OCC)c(Br)cc2c1Nc1ccc(F)cc1F | CCOC(=O)c1cnc2cc(OCC)c(N3CCN(C(C)C)CC3)cc2c1Nc1ccc(F)cc1F | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 98c8ae975f310a76e6895ad2c03786dcf0895f15908d93475fb9e11cf83466fa | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(Nc2ccnc3ccc(N4CCNCC4)cc23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1-[#8:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#7;a:5]:[c:4]1:[c:6]:[c:7](-[#8:8]):[c;H0;D3;+0:1](-[N;H0;D3;+0:12]2-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-2):[c:2]:[c:3]:1 | 65.39 | [{"value": 65.39, "product": "CCOC1=C(C=C2C(=C1)N=CC(=C2NC3=C(C=C(C=C3)F)F)C(=O)OCC)N4CCN(CC4)C(C)C", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | To a solution of ethyl 6-bromo-4-(2,4-difluorophenylamino)-7-ethoxyquinoline-3-carboxylate (400 mg, 0.89 mmol) and 1-(Isopropyl)piperazine (254 µl, 1.77 mmol) in dioxane was added cesium carbonate (722 mg, 2.22 mmol), tris(dibenzylideneacetone)dipalladium(0) (40.6 mg, 0.04 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | 110 | null | CC(C)N1CCNCC1.CCOC(=O)c1cnc2cc(OCC)c(Br)cc2c1Nc1ccc(F)cc1F>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]>CCOC(=O)... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1169cbe9fa064a879ac34b2e524a4e69 | COC(=O)c1cc2c(ncn2C)c(F)c1N.Ic1ccccc1>>COC(=O)c1cc2c(ncn2C)c(F)c1Nc1ccccc1 | C1=CC=C(C=C1)I.CN1C=NC2=C1C=C(C(=C2F)N)C(=O)OC>>CN1C=NC2=C1C=C(C(=C2F)NC3=CC=CC=C3)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([n:9][cH:10][n:11]2[CH3:12])[c:13]([F:14])[c:15]1[NH2:16].I[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([n:9][cH:10][n:11]2[CH3:12])[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | COC(=O)c1cc2c(ncn2C)c(F)c1N.Ic1ccccc1 | COC(=O)c1cc2c(ncn2C)c(F)c1Nc1ccccc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | COC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccc3[nH]cnc3c2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]-[C:12](-[#8:13])=[O;D1;H0:14]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[NH;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:11]-[C:12](-[#8:13])=[O;D1;H0:14] | 57.47 | [{"value": 57.47, "product": "CN1C=NC2=C1C=C(C(=C2F)NC3=CC=CC=C3)C(=O)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (441 mg, 0.76 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (279 mg, 0.30 mmol) were added to a round bottom flask which was evacuated and flushed with nitrogen 3 times, anisole (16.600 ml) was added and the mixture evacuated and flushed with nitrogen 3 times and the... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccccc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COC1=CC=CC=C1 | 100 | null | COC(=O)c1cc2c(ncn2C)c(F)c1N.Ic1ccccc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COC1=CC=CC=C1>COC(=O)c1cc2c(ncn2C)c(F)c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-13992005c22d4673aa802b5e140076e8 | COC(=O)c1cc2c(ncn2C)c(F)c1N.Ic1ccccc1>>COC(=O)c1cc2c(ncn2C)c(F)c1Nc1ccccc1 | C1=CC=C(C=C1)I.CN1C=NC2=C1C=C(C(=C2F)N)C(=O)OC>>CN1C=NC2=C1C=C(C(=C2F)NC3=CC=CC=C3)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([n:9][cH:10][n:11]2[CH3:12])[c:13]([F:14])[c:15]1[NH2:16].I[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([n:9][cH:10][n:11]2[CH3:12])[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | COC(=O)c1cc2c(ncn2C)c(F)c1N.Ic1ccccc1 | COC(=O)c1cc2c(ncn2C)c(F)c1Nc1ccccc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | COC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccc3[nH]cnc3c2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]-[C:12](-[#8:13])=[O;D1;H0:14]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[NH;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:11]-[C:12](-[#8:13])=[O;D1;H0:14] | 65.43 | [{"value": 65.43, "product": "CN1C=NC2=C1C=C(C(=C2F)NC3=CC=CC=C3)C(=O)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (389 mg, 0.67 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (246 mg, 0.27 mmol) were added to a round bottom flask which was evacuated and flushed with nitrogen 3 times, anisole (14.900 ml) was added and the mixture evacuated and flushed with nitrogen 3 times and the... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccccc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COC1=CC=CC=C1 | 100 | null | COC(=O)c1cc2c(ncn2C)c(F)c1N.Ic1ccccc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COC1=CC=CC=C1>COC(=O)c1cc2c(ncn2C)c(F)c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a36b48917c9942d1a34637511773ee1f | COC(=O)c1cc2c(ncn2C)c(F)c1N.Ic1ccccc1>>COC(=O)c1cc2c(ncn2C)c(F)c1Nc1ccccc1 | C1=CC=C(C=C1)I.CN1C=NC2=C1C=C(C(=C2F)N)C(=O)OC>>CN1C=NC2=C1C=C(C(=C2F)NC3=CC=CC=C3)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([n:9][cH:10][n:11]2[CH3:12])[c:13]([F:14])[c:15]1[NH2:16].I[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([n:9][cH:10][n:11]2[CH3:12])[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | COC(=O)c1cc2c(ncn2C)c(F)c1N.Ic1ccccc1 | COC(=O)c1cc2c(ncn2C)c(F)c1Nc1ccccc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | COC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccc3[nH]cnc3c2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]-[C:12](-[#8:13])=[O;D1;H0:14]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[NH;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:11]-[C:12](-[#8:13])=[O;D1;H0:14] | 75.07 | [{"value": 75.07, "product": "CN1C=NC2=C1C=C(C(=C2F)NC3=CC=CC=C3)C(=O)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (389 mg, 0.67 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (246 mg, 0.27 mmol) were added to a round bottom flask which was evacuated and flushed with nitrogen 3 times, anisole (14.900 ml) was added and the mixture evacuated and flushed with nitrogen 3 times and the... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccccc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COC1=CC=CC=C1 | 100 | null | COC(=O)c1cc2c(ncn2C)c(F)c1N.Ic1ccccc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COC1=CC=CC=C1>COC(=O)c1cc2c(ncn2C)c(F)c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5fc624fd97b7430eafbe8dcc049d170b | Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1.Nc1ccc(S(N)(=O)=O)cc1>>Cc1ccc(Oc2ccnc(Nc3ccc(S(N)(=O)=O)cc3)c2)c(C)n1 | CC1=NC(=C(C=C1)OC2=CC(=NC=C2)Cl)C.C1=CC(=CC=C1N)S(=O)(=O)N>>CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)N)C | Cl[c:11]1[n:10][cH:9][cH:8][c:7]([O:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:26][c:24]2[CH3:25])[cH:23]1.[NH2:12][c:13]1[cH:14][cH:15][c:16]([S:17]([NH2:18])(=[O:19])=[O:20])[cH:21][cH:22]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]([S:17]([NH2:18])(=[O:19])=[O:20... | Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1.Nc1ccc(S(N)(=O)=O)cc1 | Cc1ccc(Oc2ccnc(Nc3ccc(S(N)(=O)=O)cc3)c2)c(C)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(Oc3cccnc3)ccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:9] | 46.32 | [{"value": 46.32, "product": "CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)N)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | 3-(2-chloropyridin-4-yloxy)-2,6-dimethylpyridine (6.47 g, 27.57 mmol), Sulfanilamide (6.17 g, 35.84 mmol), CESIUM CARBONATE (13.47 g, 41.35 mmol) and XANTPHOS (1.595 g, 2.76 mmol) were stirred in DMA (130 ml). Purged this stirred mixture by bubbling nitrogen through for an hour, then added the Palladium acetate. Heate... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccncc1.c1ccccc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 150 | null | Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1.Nc1ccc(S(N)(=O)=O)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>Cc1ccc(Oc2ccnc(Nc3ccc(S(N)(=O)=O)cc3)c2)c(C)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c34e3f2a76e4462999414a169b276944 | Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1.Nc1ccc(S(N)(=O)=O)cc1>>Cc1ccc(Oc2ccnc(Nc3ccc(S(N)(=O)=O)cc3)c2)c(C)n1 | CC1=NC(=C(C=C1)OC2=CC(=NC=C2)Cl)C.C1=CC(=CC=C1N)S(=O)(=O)N>>CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)N)C | Cl[c:11]1[n:10][cH:9][cH:8][c:7]([O:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:26][c:24]2[CH3:25])[cH:23]1.[NH2:12][c:13]1[cH:14][cH:15][c:16]([S:17]([NH2:18])(=[O:19])=[O:20])[cH:21][cH:22]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]([S:17]([NH2:18])(=[O:19])=[O:20... | Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1.Nc1ccc(S(N)(=O)=O)cc1 | Cc1ccc(Oc2ccnc(Nc3ccc(S(N)(=O)=O)cc3)c2)c(C)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(Oc3cccnc3)ccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:9] | 76.03 | [{"value": 76.03, "product": "CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)N)C", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | XANTPHOS (2.466 g, 4.26 mmol) was added to 3-(2-chloropyridin-4-yloxy)-2,6-dimethylpyridine (10g, 42.61 mmol), Sulfanilamide (9.54 g, 55.39 mmol) and CESIUM CARBONATE (20.83 g, 63.92 mmol) in DMA (200 ml) at 20ºC. Nitrogen was bubbled through the reaction mixture for 1 hour then PALLADIUM(II) ACETATE (0.670 g, 2.98 mmo... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccncc1.c1ccccc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 130 | null | Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1.Nc1ccc(S(N)(=O)=O)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>Cc1ccc(Oc2ccnc(Nc3ccc(S(N)(=O)=O)cc3)c2)c(C)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5853dba403864121802609ae67a6fbe4 | Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1.Nc1ccc(S(N)(=O)=O)cc1>>Cc1ccc(Oc2ccnc(Nc3ccc(S(N)(=O)=O)cc3)c2)c(C)n1 | CC1=NC(=C(C=C1)OC2=CC(=NC=C2)Cl)C.C1=CC(=CC=C1N)S(=O)(=O)N>>CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)N)C | Cl[c:11]1[n:10][cH:9][cH:8][c:7]([O:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:26][c:24]2[CH3:25])[cH:23]1.[NH2:12][c:13]1[cH:14][cH:15][c:16]([S:17]([NH2:18])(=[O:19])=[O:20])[cH:21][cH:22]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]([S:17]([NH2:18])(=[O:19])=[O:20... | Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1.Nc1ccc(S(N)(=O)=O)cc1 | Cc1ccc(Oc2ccnc(Nc3ccc(S(N)(=O)=O)cc3)c2)c(C)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(Oc3cccnc3)ccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:9] | 40.86 | [{"value": 40.86, "product": "CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)N)C", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | 3-(2-chloropyridin-4-yloxy)-2,6-dimethylpyridine (2 g, 8.52 mmol), Sulfanilamide (1.91 g, 11.09 mmol), CESIUM CARBONATE (4.17 g, 12.80 mmol) and XANTPHOS (490 mg, 0.85 mmol) were stirred in DMA (40 ml). Purged this stirred mixture by bubbling nitrogen through for an hour, then added the Palladium acetate. Heated to 13... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccncc1.c1ccccc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 130 | null | Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1.Nc1ccc(S(N)(=O)=O)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>Cc1ccc(Oc2ccnc(Nc3ccc(S(N)(=O)=O)cc3)c2)c(C)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-0c597cbe4940491092243bda6c97b98c | Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1.Nc1ccc(S(N)(=O)=O)cc1>>Cc1ccc(Oc2ccnc(Nc3ccc(S(N)(=O)=O)cc3)c2)c(C)n1 | CC1=NC(=C(C=C1)OC2=CC(=NC=C2)Cl)C.C1=CC(=CC=C1N)S(=O)(=O)N>>CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)N)C | Cl[c:11]1[n:10][cH:9][cH:8][c:7]([O:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:26][c:24]2[CH3:25])[cH:23]1.[NH2:12][c:13]1[cH:14][cH:15][c:16]([S:17]([NH2:18])(=[O:19])=[O:20])[cH:21][cH:22]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]([S:17]([NH2:18])(=[O:19])=[O:20... | Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1.Nc1ccc(S(N)(=O)=O)cc1 | Cc1ccc(Oc2ccnc(Nc3ccc(S(N)(=O)=O)cc3)c2)c(C)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(Oc3cccnc3)ccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:9] | 62.38 | [{"value": 62.38, "product": "CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)N)C", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | XANTPHOS (1.603 g, 2.77 mmol) was added to 3-(2-chloropyridin-4-yloxy)-2,6-dimethylpyridine (6.5 g, 27.70 mmol), Sulfanilamide (6.20 g, 36.01 mmol) and CESIUM CARBONATE (13.54 g, 41.55 mmol) in DMA (130 ml) at 20ºC. Nitrogen was bubbled through the reaction mixture for 1 hour then PALLADIUM(II) ACETATE (0.435 g, 1.94 m... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccncc1.c1ccccc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 130 | null | Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1.Nc1ccc(S(N)(=O)=O)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>Cc1ccc(Oc2ccnc(Nc3ccc(S(N)(=O)=O)cc3)c2)c(C)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b3c4a680709749268aeba07b670223ef | Brc1cncc(Br)c1.CC(=O)N1CCNCC1>>CC(=O)N1CCN(c2cncc(Br)c2)CC1 | C1=C(C=NC=C1Br)Br.CC(=O)N1CCNCC1>>CC(=O)N1CCN(CC1)C2=CC(=CN=C2)Br | Br[c:8]1[cH:9][n:10][cH:11][c:12]([Br:13])[cH:14]1.[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][NH:7][CH2:15][CH2:16]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][n:10][cH:11][c:12]([Br:13])[cH:14]2)[CH2:15][CH2:16]1 | Brc1cncc(Br)c1.CC(=O)N1CCNCC1 | CC(=O)N1CCN(c2cncc(Br)c2)CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | fa523b05de53c4b0abc4cfee73617ebc93929b0985f4e85a4f5201b7c9df83f1 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCNCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7:7]1-[C:8]-[C:9]-[N;H0;D3;+0:10](-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:2)-[C:11]-[C:12]-1 | 31.78 | [{"value": 31.78, "product": "CC(=O)N1CCN(CC1)C2=CC(=CN=C2)Br", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | 3,5-dibromopyridine (1.233 g, 5.20 mmol), 1-(piperazin-1-yl)ethanone (0.734 g, 5.73 mmol), PdOAc2 (0.117 g, 0.52 mmol), XANTPHOS (0.361 g, 0.62 mmol), Cs2CO3 (5.09 g, 15.61 mmol), 1,4-dioxane as added to a 10 mL microwave vial. This was degassed and refilled with N2 and then heated at 140 °C in microwave for 1h. LCMS ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.c1ccncc1 | C1C[NH]CC[NH]1.c1ccncc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | 140 | null | Brc1cncc(Br)c1.CC(=O)N1CCNCC1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd]>CC(=O)N1CCN(c2cncc(Br)c2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-fa122fe6774f45c5b7a107c1460052d3 | CN1Cc2ccc(Cl)nc2OC(c2ccccc2)C1.Nc1ccc(-n2ccnc2)cc1>>CN1Cc2ccc(Nc3ccc(-n4ccnc4)cc3)nc2OC(c2ccccc2)C1 | CN1CC(OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.C1=CC(=CC=C1N)N2C=CN=C2>>CN1CC(OC2=C(C1)C=CC(=N2)NC3=CC=C(C=C3)N4C=CN=C4)C5=CC=CC=C5 | Cl[c:7]1[cH:6][cH:5][c:4]2[c:21]([n:20]1)[O:22][CH:23]([c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[CH2:30][N:2]([CH3:1])[CH2:3]2.[NH2:8][c:9]1[cH:10][cH:11][c:12](-[n:13]2[cH:14][cH:15][n:16][cH:17]2)[cH:18][cH:19]1>>[CH3:1][N:2]1[CH2:3][c:4]2[cH:5][cH:6][c:7]([NH:8][c:9]3[cH:10][cH:11][c:12](-[n:13]4[cH:14][cH:15][n:... | CN1Cc2ccc(Cl)nc2OC(c2ccccc2)C1.Nc1ccc(-n2ccnc2)cc1 | CN1Cc2ccc(Nc3ccc(-n4ccnc4)cc3)nc2OC(c2ccccc2)C1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(C2CNCc3ccc(Nc4ccc(-n5ccnc5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 41.47 | [{"value": 41.47, "product": "CN1CC(OC2=C(C1)C=CC(=N2)NC3=CC=C(C=C3)N4C=CN=C4)C5=CC=CC=C5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | [Reactants], 8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.120 g, 0.44 mmol), Palladium(II) acetate (9.81 mg, 0.04 mmol), 2-(Dicyclohexylphosphino)biphenyl (0.015 g, 0.04 mmol) and Cesium carbonate (0.427 g, 1.31 mmol) in DME (2.5 mL) were placed in a microwave vial and flushed with argon.... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2.c1ccccc1.c1c[nH]cn1.c1ccccc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1Cc2ccc(Cl)nc2OC(c2ccccc2)C1.Nc1ccc(-n2ccnc2)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>CN1Cc2ccc(Nc3ccc(-n4ccnc4)cc3)nc2OC(c2ccccc2)C1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8ce809cf74f44b02a581dcd94f0c1ae0 | CC(=O)N1Cc2ccc(Cl)nc2OC(c2cccnc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>>COc1cc(Nc2ccc3c(n2)OC(c2cccnc2)CN(C(C)=O)C3)ccc1-n1cnc(C)c1 | CC(=O)N1CC(OC2=C(C1)C=CC(=N2)Cl)C3=CN=CC=C3.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)C5=CN=CC=C5)C(=O)C)C=C3)OC | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([c:15]1[cH:16][cH:17][cH:18][n:19][cH:20]1)[CH2:21][N:22]([C:23]([CH3:24])=[O:25])[CH2:26]2.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:27][cH:28][c:29]1-[n:30]1[cH:31][n:32][c:33]([CH3:34])[cH:35]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11... | CC(=O)N1Cc2ccc(Cl)nc2OC(c2cccnc2)C1.COc1cc(N)ccc1-n1cnc(C)c1 | COc1cc(Nc2ccc3c(n2)OC(c2cccnc2)CN(C(C)=O)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(C2CNCc3ccc(Nc4ccc(-n5ccnc5)cc4)nc3O2)c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 35.13 | [{"value": 35.13, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)C5=CN=CC=C5)C(=O)C)C=C3)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 1-(8-chloro-2-(pyridin-3-yl)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanone (0.043 g, 0.14 mmol), Palladium(II) acetate (3.18 mg, 0.01 mmol), 2-(Dicyclohexylphosphino)biphenyl (4.96 mg, 0.01 mmol) and Cesium carbonate (0.138 g, 0.42 mmol) were placed in a microwave vial and flushed with argon. DME (2 mL) was a... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1ccncc1.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CC(=O)N1Cc2ccc(Cl)nc2OC(c2cccnc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1cc(Nc2ccc3c(n2)OC(c2cccnc2)CN(C(C)=O)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-373fd601db1247b0b18c34bca387c3a4 | CN1Cc2ccc(Cl)nc2OC(c2cccnc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>>COc1cc(Nc2ccc3c(n2)OC(c2cccnc2)CN(C)C3)ccc1-n1cnc(C)c1 | CN1CC(OC2=C(C1)C=CC(=N2)Cl)C3=CN=CC=C3.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)C5=CN=CC=C5)C)C=C3)OC | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([c:15]1[cH:16][cH:17][cH:18][n:19][cH:20]1)[CH2:21][N:22]([CH3:23])[CH2:24]2.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:25][cH:26][c:27]1-[n:28]1[cH:29][n:30][c:31]([CH3:32])[cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12]2)[O:13... | CN1Cc2ccc(Cl)nc2OC(c2cccnc2)C1.COc1cc(N)ccc1-n1cnc(C)c1 | COc1cc(Nc2ccc3c(n2)OC(c2cccnc2)CN(C)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(C2CNCc3ccc(Nc4ccc(-n5ccnc5)cc4)nc3O2)c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 27.8 | [{"value": 27.8, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)C5=CN=CC=C5)C)C=C3)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | [Reactants], Palladium(II) acetate (5.29 mg, 0.02 mmol), 2-(Dicyclohexylphosphino)biphenyl (8.26 mg, 0.02 mmol) and Cesium carbonate (0.230 g, 0.71 mmol) were placed in a microwave vial and flushed with argon. DME (2 mL) was added and the reaction mixture was run in the microwave at 100°C for 60 minutes. Reaction not c... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1ccncc1.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1Cc2ccc(Cl)nc2OC(c2cccnc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1cc(Nc2ccc3c(n2)OC(c2cccnc2)CN(C)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-79caf81165b848e5b1765189056bb075 | CC(C)(C)OC(N)=O.Fc1ccnc(Cl)c1>>CC(C)(C)OC(=O)Nc1cc(F)ccn1 | C1=CN=C(C=C1F)Cl.CC(C)(C)OC(=O)N>>CC(C)(C)OC(=O)NC1=NC=CC(=C1)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH2:8].Cl[c:9]1[cH:10][c:11]([F:12])[cH:13][cH:14][n:15]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][c:11]([F:12])[cH:13][cH:14][n:15]1 | CC(C)(C)OC(N)=O.Fc1ccnc(Cl)c1 | CC(C)(C)OC(=O)Nc1cc(F)ccn1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | ed01b145192f9cffb3f3553513f8bbd15ca4f246fc1ccc0dad392a1f0f7069ce | 23f4e0d8af1d86d8b907685b9e69e28ed17e2c9c83b8194f1d8a52eb89f58564 | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](-[NH2;D1;+0:12])=[O;D1;H0:13]>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:13])-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 19.46 | [{"value": 19.46, "product": "CC(C)(C)OC(=O)NC1=NC=CC(=C1)F", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | 2-chloro-4-fluoropyridine (132 mg, 1 mmol), tert-butyl carbamate (123 mg, 1.05 mmol), CESIUM CARBONATE (652 mg, 2.00 mmol) ,TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (36.6 mg, 0.04 mmol) and 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE (46.3 mg, 0.08 mmol) were suspended in 1,4-dioxane (2.5 ml) ,degased with argon and h... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester | Carbamic ester | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 90 | null | CC(C)(C)OC(N)=O.Fc1ccnc(Cl)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CC(C)(C)OC(=O)Nc1cc(F)ccn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-4695ad3979554c448a445867cc030440 | COc1cc(C=O)ccc1N.Clc1ncc(Cl)c(-c2cnc3ccccn23)n1>>COc1cc(C=O)ccc1Nc1ncc(Cl)c(-c2cnc3ccccn23)n1 | C1=CC2=NC=C(N2C=C1)C3=NC(=NC=C3Cl)Cl.COC1=C(C=CC(=C1)C=O)N>>COC1=C(C=CC(=C1)C=O)NC2=NC=C(C(=N2)C3=CN=C4N3C=CC=C4)Cl | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][cH:9][c:10]1[NH2:11].Cl[c:12]1[n:13][cH:14][c:15]([Cl:16])[c:17](-[c:18]2[cH:19][n:20][c:21]3[cH:22][cH:23][cH:24][cH:25][n:26]23)[n:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][cH:9][c:10]1[NH:11][c:12]1[n:13][cH:14][c:15]([Cl:16])[c:17](-[c:18]2[cH:19][n:20... | COc1cc(C=O)ccc1N.Clc1ncc(Cl)c(-c2cnc3ccccn23)n1 | COc1cc(C=O)ccc1Nc1ncc(Cl)c(-c2cnc3ccccn23)n1 | C1CCC2=NCCCN2CC1 | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(-c3cnc4ccccn34)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | 34.9 | [{"value": 34.9, "product": "COC1=C(C=CC(=C1)C=O)NC2=NC=C(C(=N2)C3=CN=C4N3C=CC=C4)Cl", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | 3-(2,5-dichloropyrimidin-4-yl)imidazo[1,2-a]pyridine (4 g, 15.09 mmol), 4-amino-3-methoxybenzaldehyde (2.281 g, 15.09 mmol), 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE (0.873 g, 1.51 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (0.345 g, 0.38 mmol) and 1,8-DIAZABICYCLO [5.4.0] UNDEC-7-ENE (5.64 ml, 37.72 mmol) wer... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccn2ccnc2c1 | HCl | C1CCC2=NCCCN2CC1.CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 120 | null | COc1cc(C=O)ccc1N.Clc1ncc(Cl)c(-c2cnc3ccccn23)n1>C1CCC2=NCCCN2CC1.CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>COc1cc(C=O)ccc1Nc1ncc(Cl)c(-c2c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-56220a6924fb4d7e8ff752a004488872 | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br>>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 | C1COCCN1CC2=CC(=C(C=C2)Br)F.CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N>>CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F | [CH3:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][c:8]([NH2:9])[n:24][cH:25][c:26]2[F:27])[n:28]1[CH:29]1[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1.Br[c:10]1[cH:11][cH:12][c:13]([CH2:14][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[cH:21][c:22]1[F:23]>>[CH3:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][c:8]([NH:9][c:10]3[cH:11][cH:12]... | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br | Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 | CCC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(-c2cncn2C2CCOCC2)nc(Nc2ccc(CN3CCOCC3)cc2)n1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]):[c:2]:[c:3] | 81 | [{"value": 81.0, "product": "CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | The aim of the reaction is test/optimization: 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (100 mg, 0.36 mmol), 4-(4-bromo-3-fluorobenzyl)morpholine (109 mg, 0.40 mmol), Palladium, 10% On Charcoal (115 mg, 0.11 mmol), racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (101 mg, ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1c[nH]cn1.c1cncnc1.c1ccccc1.C1COCC[NH]1.C1CCOCC1 | HBr | CCC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.[Pd].CC1=CC=CC=C1 | 110 | null | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br>CCC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.[Pd].CC1=CC=CC=C1>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b9ea1ddb99074c47af3b567d6c34306c | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br>>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 | C1COCCN1CC2=CC(=C(C=C2)Br)F.CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N>>CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F | [CH3:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][c:8]([NH2:9])[n:24][cH:25][c:26]2[F:27])[n:28]1[CH:29]1[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1.Br[c:10]1[cH:11][cH:12][c:13]([CH2:14][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[cH:21][c:22]1[F:23]>>[CH3:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][c:8]([NH:9][c:10]3[cH:11][cH:12]... | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br | Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 | CCC(C)(C)[O-].[Na+] | CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(-c2cncn2C2CCOCC2)nc(Nc2ccc(CN3CCOCC3)cc2)n1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]):[c:2]:[c:3] | 88 | [{"value": 88.0, "product": "CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | The aim of the reaction is test/optimization: 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (100 mg, 0.36 mmol), 4-(4-bromo-3-fluorobenzyl)morpholine (109 mg, 0.40 mmol), Palladium, 10% On Charcoal (115 mg, 0.11 mmol), Tri-o-tolylphosphine (49.4 mg, 0.16 mmol) and Sodium tert-pen... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1c[nH]cn1.c1cncnc1.c1ccccc1.C1COCC[NH]1.C1CCOCC1 | HBr | CCC(C)(C)[O-].[Na+].CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C.[Pd].CC1=CC=CC=C1 | 110 | null | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br>CCC(C)(C)[O-].[Na+].CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C.[Pd].CC1=CC=CC=C1>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-572b233d6c664fada44bd8d3bb48fc2f | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br>>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 | C1COCCN1CC2=CC(=C(C=C2)Br)F.CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N>>CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F | [CH3:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][c:8]([NH2:9])[n:24][cH:25][c:26]2[F:27])[n:28]1[CH:29]1[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1.Br[c:10]1[cH:11][cH:12][c:13]([CH2:14][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[cH:21][c:22]1[F:23]>>[CH3:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][c:8]([NH:9][c:10]3[cH:11][cH:12]... | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br | Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 | CCC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(-c2cncn2C2CCOCC2)nc(Nc2ccc(CN3CCOCC3)cc2)n1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]):[c:2]:[c:3] | 73 | [{"value": 73.0, "product": "CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | The aim of the reaction is test/optimization: 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (100 mg, 0.36 mmol), 4-(4-bromo-3-fluorobenzyl)morpholine (109 mg, 0.40 mmol), Palladium, 10% On Charcoal (115 mg, 0.11 mmol), Triphenylphosphine (0.038 mL, 0.16 mmol) and Sodium tert-pent... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1c[nH]cn1.c1cncnc1.c1ccccc1.C1COCC[NH]1.C1CCOCC1 | HBr | CCC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd].CC1=CC=CC=C1 | 110 | null | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br>CCC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd].CC1=CC=CC=C1>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2c710cb7fbbd4d70b492cf6ab2e6cbf5 | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br>>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 | C1COCCN1CC2=CC(=C(C=C2)Br)F.CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N>>CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F | [CH3:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][c:8]([NH2:9])[n:24][cH:25][c:26]2[F:27])[n:28]1[CH:29]1[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1.Br[c:10]1[cH:11][cH:12][c:13]([CH2:14][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[cH:21][c:22]1[F:23]>>[CH3:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][c:8]([NH:9][c:10]3[cH:11][cH:12]... | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br | Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 | CCC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(-c2cncn2C2CCOCC2)nc(Nc2ccc(CN3CCOCC3)cc2)n1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]):[c:2]:[c:3] | 79 | [{"value": 79.0, "product": "CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | The aim of the reaction is test/optimization: 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (100 mg, 0.36 mmol), 4-(4-bromo-3-fluorobenzyl)morpholine (109 mg, 0.40 mmol), Palladium, 10% On Charcoal (115 mg, 0.11 mmol), (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1c[nH]cn1.c1cncnc1.c1ccccc1.C1COCC[NH]1.C1CCOCC1 | HBr | CCC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].[Pd].CC1=CC=CC=C1 | 110 | null | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br>CCC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].[Pd].CC1=CC=CC=C1>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ea29507936c14849a1aa88403efb7090 | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br>>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 | C1COCCN1CC2=CC(=C(C=C2)Br)F.CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N>>CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F | [CH3:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][c:8]([NH2:9])[n:24][cH:25][c:26]2[F:27])[n:28]1[CH:29]1[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1.Br[c:10]1[cH:11][cH:12][c:13]([CH2:14][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[cH:21][c:22]1[F:23]>>[CH3:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][c:8]([NH:9][c:10]3[cH:11][cH:12]... | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br | Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 | CCC(C)(C)[O-].[Na+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(-c2cncn2C2CCOCC2)nc(Nc2ccc(CN3CCOCC3)cc2)n1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]):[c:2]:[c:3] | 85 | [{"value": 85.0, "product": "CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | The aim of the reaction is test/optimization: 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (100 mg, 0.36 mmol), 4-(4-bromo-3-fluorobenzyl)morpholine (109 mg, 0.40 mmol), Palladium, 10% On Charcoal (115 mg, 0.11 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (94 mg, 0.16 ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1c[nH]cn1.c1cncnc1.c1ccccc1.C1COCC[NH]1.C1CCOCC1 | HBr | CCC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.[Pd].CC1=CC=CC=C1 | 110 | null | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br>CCC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.[Pd].CC1=CC=CC=C1>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-28a0ca5c779744199b5c278aec8fa826 | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br>>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 | C1COCCN1CC2=CC(=C(C=C2)Br)F.CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N>>CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F | [CH3:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][c:8]([NH2:9])[n:24][cH:25][c:26]2[F:27])[n:28]1[CH:29]1[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1.Br[c:10]1[cH:11][cH:12][c:13]([CH2:14][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[cH:21][c:22]1[F:23]>>[CH3:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][c:8]([NH:9][c:10]3[cH:11][cH:12]... | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br | Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 | CCC(C)(C)[O-].[Na+] | COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(-c2cncn2C2CCOCC2)nc(Nc2ccc(CN3CCOCC3)cc2)n1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]):[c:2]:[c:3] | 85 | [{"value": 85.0, "product": "CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | The aim of the reaction is test/optimization: 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (100 mg, 0.36 mmol), 4-(4-bromo-3-fluorobenzyl)morpholine (109 mg, 0.40 mmol), Palladium, 10% On Charcoal (115 mg, 0.11 mmol), 2-Dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl (66.6 m... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1c[nH]cn1.c1cncnc1.c1ccccc1.C1COCC[NH]1.C1CCOCC1 | HBr | CCC(C)(C)[O-].[Na+].COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.[Pd].CC1=CC=CC=C1 | 110 | null | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br>CCC(C)(C)[O-].[Na+].COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.[Pd].CC1=CC=CC=C1>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3e57b5a0d75c4f5d9c22ce74626f60c3 | CC(=O)Nc1cc(Cl)ccn1.Nc1c(Cl)ccc2c1OCO2>>CC(=O)Nc1cc(Nc2c(Cl)ccc3c2OCO3)ccn1 | CC(=O)NC1=NC=CC(=C1)Cl.C1OC2=C(O1)C(=C(C=C2)Cl)N>>CC(=O)NC1=NC=CC(=C1)NC2=C(C=CC3=C2OCO3)Cl | Cl[c:7]1[cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[n:21][cH:20][cH:19]1.[NH2:8][c:9]1[c:10]([Cl:11])[cH:12][cH:13][c:14]2[c:15]1[O:16][CH2:17][O:18]2>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[c:10]([Cl:11])[cH:12][cH:13][c:14]3[c:15]2[O:16][CH2:17][O:18]3)[cH:19][cH:20][n:21]1 | CC(=O)Nc1cc(Cl)ccn1.Nc1c(Cl)ccc2c1OCO2 | CC(=O)Nc1cc(Nc2c(Cl)ccc3c2OCO3)ccn1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccncc2)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9]):[c:10]:1.[#8:11]-[c:12]:[c:13](-[NH2;D1;+0:14]):[c:15]>>[#8:11]-[c:12]:[c:13](-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9]):[c:10]:1):[c:15] | 83.06 | [{"value": 83.06, "product": "CC(=O)NC1=NC=CC(=C1)NC2=C(C=CC3=C2OCO3)Cl", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | Reaction carried out in two batches in 20 ml microwave tubes. 5-chlorobenzo[d][1,3]dioxol-4-amine (1 g, 5.83 mmol), N-(4-chloropyridin-2-yl)acetamide (0.994 g, 5.83 mmol), XANTPHOS (0.405 g, 0.70 mmol), PALLADIUM(II) ACETATE (0.065 g, 0.29 mmol) and CESIUM CARBONATE (3.80 g, 11.66 mmol) were suspended in 2x DMA (12mL) ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccc2c(c1)OCO2 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 150 | null | CC(=O)Nc1cc(Cl)ccn1.Nc1c(Cl)ccc2c1OCO2>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>CC(=O)Nc1cc(Nc2c(Cl)ccc3c2OCO3)ccn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-bc24f3de1ac64e7e96966f7efd955e5c | CN1CCc2cccc(N)c2C1=O.Clc1cc(I)c(Cl)cn1>>CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O | C1=C(C(=CN=C1Cl)Cl)I.CN1CCC2=C(C1=O)C(=CC=C2)N>>CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl | [CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH2:10])[c:19]2[C:20]1=[O:21].I[c:11]1[cH:12][c:13]([Cl:14])[n:15][cH:16][c:17]1[Cl:18]>>[CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[cH:12][c:13]([Cl:14])[n:15][cH:16][c:17]3[Cl:18])[c:19]2[C:20]1=[O:21] | CN1CCc2cccc(N)c2C1=O.Clc1cc(I)c(Cl)cn1 | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCc2cccc(Nc3ccncc3)c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8].[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13](-[NH2;D1;+0:14]):[c:15]>>[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13](-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8]):[c:15] | 42.5 | [{"value": 42.5, "product": "CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (0.205 g, 0.91 mmol) was added to a stirred suspension of 2,5-dichloro-4-iodopyridine (5 g, 18.26 mmol), 8-amino-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (3.22 g, 18.26 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.056 g, 1.83 mmol) and cesium carbonate (8.92 g, 27.38 mmol) dis... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccc2c(c1)CC[NH]C2.c1ccncc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CN1CCc2cccc(N)c2C1=O.Clc1cc(I)c(Cl)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-702aadae7425481bab668d630b5a0a21 | CN1CCc2cccc(N)c2C1=O.Clc1cc(I)c(Cl)cn1>>CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O | C1=C(C(=CN=C1Cl)Cl)I.CN1CCC2=C(C1=O)C(=CC=C2)N>>CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl | [CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH2:10])[c:19]2[C:20]1=[O:21].I[c:11]1[cH:12][c:13]([Cl:14])[n:15][cH:16][c:17]1[Cl:18]>>[CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[cH:12][c:13]([Cl:14])[n:15][cH:16][c:17]3[Cl:18])[c:19]2[C:20]1=[O:21] | CN1CCc2cccc(N)c2C1=O.Clc1cc(I)c(Cl)cn1 | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCc2cccc(Nc3ccncc3)c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8].[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13](-[NH2;D1;+0:14]):[c:15]>>[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13](-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8]):[c:15] | 63.33 | [{"value": 63.33, "product": "CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (24.59 mg, 0.11 mmol) was added to a stirred suspension of 2,5-dichloro-4-iodopyridine (600 mg, 2.19 mmol), 8-amino-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (386 mg, 2.19 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (127 mg, 0.22 mmol) and cesium carbonate (1071 mg, 3.29 mmol) in... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccc2c(c1)CC[NH]C2.c1ccncc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CN1CCc2cccc(N)c2C1=O.Clc1cc(I)c(Cl)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b62d19842af048f4873fe9a01ff50f3b | CN1CCc2cccc(N)c2C1=O.Clc1cc(I)c(Cl)cn1>>CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O | C1=C(C(=CN=C1Cl)Cl)I.CN1CCC2=C(C1=O)C(=CC=C2)N>>CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl | [CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH2:10])[c:19]2[C:20]1=[O:21].I[c:11]1[cH:12][c:13]([Cl:14])[n:15][cH:16][c:17]1[Cl:18]>>[CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[cH:12][c:13]([Cl:14])[n:15][cH:16][c:17]3[Cl:18])[c:19]2[C:20]1=[O:21] | CN1CCc2cccc(N)c2C1=O.Clc1cc(I)c(Cl)cn1 | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCc2cccc(Nc3ccncc3)c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8].[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13](-[NH2;D1;+0:14]):[c:15]>>[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13](-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8]):[c:15] | 49.43 | [{"value": 49.43, "product": "CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (0.152 g, 0.68 mmol) was added to a stirred suspension of 2,5-dichloro-4-iodopyridine (3.71 g, 13.56 mmol), 8-amino-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (2.39 g, 13.56 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.785 g, 1.36 mmol) and cesium carbonate (6.63 g, 20.34 mmol) ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccc2c(c1)CC[NH]C2.c1ccncc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CN1CCc2cccc(N)c2C1=O.Clc1cc(I)c(Cl)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d1c742201cbe4cf0aa1fbc6e2537aa34 | CN1CCc2cccc(N)c2C1=O.Clc1cc(I)c(Cl)cn1>>CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O | C1=C(C(=CN=C1Cl)Cl)I.CN1CCC2=C(C1=O)C(=CC=C2)N>>CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl | [CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH2:10])[c:19]2[C:20]1=[O:21].I[c:11]1[cH:12][c:13]([Cl:14])[n:15][cH:16][c:17]1[Cl:18]>>[CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[cH:12][c:13]([Cl:14])[n:15][cH:16][c:17]3[Cl:18])[c:19]2[C:20]1=[O:21] | CN1CCc2cccc(N)c2C1=O.Clc1cc(I)c(Cl)cn1 | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCc2cccc(Nc3ccncc3)c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8].[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13](-[NH2;D1;+0:14]):[c:15]>>[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13](-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8]):[c:15] | 59.55 | [{"value": 59.55, "product": "CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (0.573 g, 2.55 mmol) was added to a stirred suspension of 2,5-dichloro-4-iodopyridine (13.99 g, 51.07 mmol), 8-amino-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (9 g, 51.07 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.96 g, 5.11 mmol) and cesium carbonate (24.96 g, 76.61 mmol) di... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccc2c(c1)CC[NH]C2.c1ccncc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CN1CCc2cccc(N)c2C1=O.Clc1cc(I)c(Cl)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f766bf8ef3f8450eb6d323fd10519896 | CONC(=O)c1ccccc1N.Clc1cc(I)c(Cl)cn1>>CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl | C1=C(C(=CN=C1Cl)Cl)I.CONC(=O)C1=CC=CC=C1N>>CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl | [CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH2:12].I[c:13]1[cH:14][c:15]([Cl:16])[n:17][cH:18][c:19]1[Cl:20]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH:12][c:13]1[cH:14][c:15]([Cl:16])[n:17][cH:18][c:19]1[Cl:20] | CONC(=O)c1ccccc1N.Clc1cc(I)c(Cl)cn1 | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncc2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8].[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13](-[NH2;D1;+0:14]):[c:15]>>[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13](-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8]):[c:15] | 39.07 | [{"value": 39.07, "product": "CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2,5-dichloro-4-iodopyridine (75 g, 273.84 mmol), 2-amino-N-methoxybenzamide (47.8 g, 287.53 mmol), cesium carbonate (107 g, 328.60 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (11.88 g, 20.54 mmol) were suspended in 1,4-dioxane (913 ml). Nitrogen was bubbled through the mixture for 20 minutes the... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CONC(=O)c1ccccc1N.Clc1cc(I)c(Cl)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-aaefdd638c464adeb91c856ec0ce39ed | CONC(=O)c1ccccc1N.Clc1cc(I)c(Cl)cn1>>CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl | C1=C(C(=CN=C1Cl)Cl)I.CONC(=O)C1=CC=CC=C1N>>CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl | [CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH2:12].I[c:13]1[cH:14][c:15]([Cl:16])[n:17][cH:18][c:19]1[Cl:20]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH:12][c:13]1[cH:14][c:15]([Cl:16])[n:17][cH:18][c:19]1[Cl:20] | CONC(=O)c1ccccc1N.Clc1cc(I)c(Cl)cn1 | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncc2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8].[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13](-[NH2;D1;+0:14]):[c:15]>>[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13](-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8]):[c:15] | 69.18 | [{"value": 69.18, "product": "CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2,5-dichloro-4-iodopyridine (10.4 g, 37.97 mmol), 2-amino-N-methoxybenzamide (6.63 g, 39.87 mmol), cesium carbonate (14.85 g, 45.57 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.648 g, 2.85 mmol) were suspended in 1,4-dioxane (130 mL). Nitrogen was bubbled through the mixture for 10 minutes the... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CONC(=O)c1ccccc1N.Clc1cc(I)c(Cl)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b94a4cbc1fbd4100843834a92096e35b | CNC(=O)c1ccccc1N.Clc1cc(I)c(Cl)cn1>>CNC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl | C1=C(C(=CN=C1Cl)Cl)I.CNC(=O)C1=CC=CC=C1N>>CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[NH2:11].I[c:12]1[cH:13][c:14]([Cl:15])[n:16][cH:17][c:18]1[Cl:19]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[NH:11][c:12]1[cH:13][c:14]([Cl:15])[n:16][cH:17][c:18]1[Cl:19] | CNC(=O)c1ccccc1N.Clc1cc(I)c(Cl)cn1 | CNC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncc2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8].[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13](-[NH2;D1;+0:14]):[c:15]>>[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13](-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8]):[c:15] | 69.36 | [{"value": 69.36, "product": "CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2-amino-N-methylbenzamide (110 mg, 0.73 mmol), 2,5-dichloro-4-iodopyridine (200 mg, 0.73 mmol), diacetoxypalladium (8.20 mg, 0.04 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (42.3 mg, 0.07 mmol) and cesium carbonate (357 mg, 1.10 mmol) suspended in 1,4-dioxane (4 mL) was weighed out in a microwave ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CNC(=O)c1ccccc1N.Clc1cc(I)c(Cl)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-36d41d697d8f415b8c7cc3a381080785 | CNC(=O)c1ccccc1N.Clc1cc(I)c(Cl)cn1>>CNC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl | C1=C(C(=CN=C1Cl)Cl)I.CNC(=O)C1=CC=CC=C1N>>CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[NH2:11].I[c:12]1[cH:13][c:14]([Cl:15])[n:16][cH:17][c:18]1[Cl:19]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[NH:11][c:12]1[cH:13][c:14]([Cl:15])[n:16][cH:17][c:18]1[Cl:19] | CNC(=O)c1ccccc1N.Clc1cc(I)c(Cl)cn1 | CNC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncc2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8].[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13](-[NH2;D1;+0:14]):[c:15]>>[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13](-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8]):[c:15] | 32.06 | [{"value": 32.06, "product": "CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | Palladium(II) acetate (0.098 g, 0.44 mmol) was added to 2,5-dichloro-4-iodopyridine (3 g, 10.95 mmol), 2-amino-N-methylbenzamide (1.645 g, 10.95 mmol), Cesium carbonate (7.14 g, 21.91 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (0.380 g, 0.66 mmol) in dioxane (150 mL) under nitrogen. The resulting suspen... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 80 | null | CNC(=O)c1ccccc1N.Clc1cc(I)c(Cl)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2a024728550642b2b2e2724a7387802d | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Cl>>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 | C1COCCN1CC2=CC(=C(C=C2)Cl)F.CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N>>CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F | [CH3:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][c:8]([NH2:9])[n:24][cH:25][c:26]2[F:27])[n:28]1[CH:29]1[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1.Cl[c:10]1[cH:11][cH:12][c:13]([CH2:14][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[cH:21][c:22]1[F:23]>>[CH3:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][c:8]([NH:9][c:10]3[cH:11][cH:12]... | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Cl | Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 | CC(C)(C)[O-].[K+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(-c2cncn2C2CCOCC2)nc(Nc2ccc(CN3CCOCC3)cc2)n1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]):[c:2]:[c:3] | 9.15 | [{"value": 9.15, "product": "CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F", "details": "", "is_desired": true}] | 102 | CELSIUS | null | null | To degassed 1,4-dioxane (13.900 ml) in a flame-dried and argonflushed 50 mL roundbottomed flask were added 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (386 mg, 1.39 mmol) and 4-(4-chloro-3-fluorobenzyl)morpholine (320 mg, 1.39 mmol) followed by POTASSIUM TERT-BUTOXIDE (203 mg, 1... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1c[nH]cn1.c1cncnc1.c1ccccc1.C1COCC[NH]1.C1CCOCC1 | HCl | CC(C)(C)[O-].[K+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 102 | null | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Cl>CC(C)(C)[O-].[K+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-68a2d19644de420ea283722f281ee146 | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Cl>>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 | C1COCCN1CC2=CC(=C(C=C2)Cl)F.CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N>>CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F | [CH3:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][c:8]([NH2:9])[n:24][cH:25][c:26]2[F:27])[n:28]1[CH:29]1[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1.Cl[c:10]1[cH:11][cH:12][c:13]([CH2:14][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[cH:21][c:22]1[F:23]>>[CH3:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][c:8]([NH:9][c:10]3[cH:11][cH:12]... | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Cl | Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1 | CC(C)(C)[O-].[K+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(-c2cncn2C2CCOCC2)nc(Nc2ccc(CN3CCOCC3)cc2)n1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]):[c:2]:[c:3] | 11.43 | [{"value": 11.43, "product": "CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F", "details": "", "is_desired": true}] | 102 | CELSIUS | null | null | To degassed 1,4-dioxane (39.2 ml) in a flame-dried and argonflushed 250 mL roundbottomed flask were added 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (1.076 g, 3.88 mmol) and 4-(4-chloro-3-fluorobenzyl)morpholine (0.9 g, 3.92 mmol) followed by POTASSIUM TERT-BUTOXIDE (0.572 g, 5... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1c[nH]cn1.c1cncnc1.c1ccccc1.C1COCC[NH]1.C1CCOCC1 | HCl | CC(C)(C)[O-].[K+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 102 | null | Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Cl>CC(C)(C)[O-].[K+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9f0febad39ec4abd95b00a68a93da5f3 | C[C@H](Nc1nc(Cl)nc(N2CCOCC2)n1)c1ncc(F)cn1.Cc1cnc(N)s1>>Cc1cnc(Nc2nc(N[C@@H](C)c3ncc(F)cn3)nc(N3CCOCC3)n2)s1 | C[C@@H](C1=NC=C(C=N1)F)NC2=NC(=NC(=N2)Cl)N3CCOCC3.CC1=CN=C(S1)N>>CC1=CN=C(S1)NC2=NC(=NC(=N2)N3CCOCC3)N[C@@H](C)C4=NC=C(C=N4)F | Cl[c:7]1[n:8][c:9]([NH:10][C@@H:11]([CH3:12])[c:13]2[n:14][cH:15][c:16]([F:17])[cH:18][n:19]2)[n:20][c:21]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[n:28]1.[CH3:1][c:2]1[cH:3][n:4][c:5]([NH2:6])[s:29]1>>[CH3:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[n:8][c:9]([NH:10][C@@H:11]([CH3:12])[c:13]3[n:14][cH:15][c:16]([F:17... | C[C@H](Nc1nc(Cl)nc(N2CCOCC2)n1)c1ncc(F)cn1.Cc1cnc(N)s1 | Cc1cnc(Nc2nc(N[C@@H](C)c3ncc(F)cn3)nc(N3CCOCC3)n2)s1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 565b1b62b297a3b1aad544a4f6d7760fc3910e7d367c9719d0e48a6d3fe6c36e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cnc(CNc2nc(Nc3nccs3)nc(N3CCOCC3)n2)nc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[#7;a:7]:1.[NH2;D1;+0:8]-[c:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9]2:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:2):[#7;a:2]:1 | 20.67 | [{"value": 20.67, "product": "CC1=CN=C(S1)NC2=NC(=NC(=N2)N3CCOCC3)N[C@@H](C)C4=NC=C(C=N4)F", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | (S)-4-chloro-N-(1-(5-fluoropyrimidin-2-yl)ethyl)-6-morpholino-1,3,5-triazin-2-amine (100 mg, 0.29 mmol), 5-methylthiazol-2-amine (50.4 mg, 0.44 mmol), BINAP (18.33 mg, 0.03 mmol), Pd2(dba)3 (13.48 mg, 0.01 mmol) and Cs2CO3 (240 mg, 0.74 mmol) were combined in a microwave reaction tube and vacuum purged. The tube was th... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ncncn1 | c1ncncn1 | c1cscn1.c1ncncn1.c1cncnc1.C1COCC[NH]1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 95 | null | C[C@H](Nc1nc(Cl)nc(N2CCOCC2)n1)c1ncc(F)cn1.Cc1cnc(N)s1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Cc1... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-80e16f813a4348d09194009ae04f2217 | CNC(=O)c1ccccc1Nc1cc(Cl)ncc1C#N.Cc1nn(C)cc1N>>CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C#N | CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C#N)Cl.CC1=NN(C=C1N)C>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NC)C#N)C | Cl[c:14]1[cH:13][c:12]([NH:11][c:10]2[c:5]([C:3]([NH:2][CH3:1])=[O:4])[cH:6][cH:7][cH:8][cH:9]2)[c:25]([C:26]#[N:27])[cH:24][n:23]1.[NH2:15][c:16]1[cH:17][n:18]([CH3:19])[n:20][c:21]1[CH3:22]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[NH:11][c:12]1[cH:13][c:14]([NH:15][c:16]2[cH:17][n:18]([CH3:19]... | CNC(=O)c1ccccc1Nc1cc(Cl)ncc1C#N.Cc1nn(C)cc1N | CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C#N | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cn[nH]c3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9](-[C;D1;H3:10]):[c:11](-[NH2;D1;+0:12]):[c:13]:1>>[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9](-[C;D1;H3:10]):[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:13]:1 | 49.98 | [{"value": 49.98, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NC)C#N)C", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | 2-(2-chloro-5-cyanopyridin-4-ylamino)-N-methylbenzamide (200 mg, 0.70 mmol), Palladium(II) acetate (12.53 mg, 0.06 mmol), 1,3-dimethyl-1H-pyrazol-4-amine (155 mg, 1.40 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (48.4 mg, 0.08 mmol) and Cesium carbonate (273 mg, 0.84 mmol) were suspended in dioxane (5 mL) in... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cn[nH]c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CNC(=O)c1ccccc1Nc1cc(Cl)ncc1C#N.Cc1nn(C)cc1N>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C#N |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d012fdccb17647d4838efd4e1491311e | CNC(=O)c1ccccc1Nc1cc(Cl)ncc1C#N.COc1cc(N)n(C)n1>>CNC(=O)c1ccccc1Nc1cc(Nc2cc(OC)nn2C)ncc1C#N | CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C#N)Cl.CN1C(=CC(=N1)OC)N>>CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C#N)NC3=CC(=NN3C)OC | Cl[c:14]1[cH:13][c:12]([NH:11][c:10]2[c:5]([C:3]([NH:2][CH3:1])=[O:4])[cH:6][cH:7][cH:8][cH:9]2)[c:26]([C:27]#[N:28])[cH:25][n:24]1.[NH2:15][c:16]1[cH:17][c:18]([O:19][CH3:20])[n:21][n:22]1[CH3:23]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[NH:11][c:12]1[cH:13][c:14]([NH:15][c:16]2[cH:17][c:18]([O... | CNC(=O)c1ccccc1Nc1cc(Cl)ncc1C#N.COc1cc(N)n(C)n1 | CNC(=O)c1ccccc1Nc1cc(Nc2cc(OC)nn2C)ncc1C#N | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 54.7 | [{"value": 54.7, "product": "CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C#N)NC3=CC(=NN3C)OC", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | 2-(2-chloro-5-cyanopyridin-4-ylamino)-N-methylbenzamide (100 mg, 0.35 mmol), Palladium(II) acetate (6.26 mg, 0.03 mmol), [Reactants], 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (24.22 mg, 0.04 mmol) and Cesium carbonate (136 mg, 0.42 mmol) were suspended in dioxane (3 mL) into a test tube. The reaction was purged ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CNC(=O)c1ccccc1Nc1cc(Cl)ncc1C#N.COc1cc(N)n(C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1ccccc1Nc1cc(Nc2cc(OC)nn2C)ncc1C#N |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2e4132c3c32149d3a68cd64301eacce5 | CN1CCc2cccc(Nc3cc(Cl)ncc3C#N)c2C1=O.Cc1nn(C)cc1N>>Cc1nn(C)cc1Nc1cc(Nc2cccc3c2C(=O)N(C)CC3)c(C#N)cn1 | CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3C#N)Cl.CC1=NN(C=C1N)C>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C#N)C | Cl[c:9]1[cH:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][c:17]3[c:18]2[C:19](=[O:20])[N:21]([CH3:22])[CH2:23][CH2:24]3)[c:25]([C:26]#[N:27])[cH:28][n:29]1.[CH3:1][c:2]1[n:3][n:4]([CH3:5])[cH:6][c:7]1[NH2:8]>>[CH3:1][c:2]1[n:3][n:4]([CH3:5])[cH:6][c:7]1[NH:8][c:9]1[cH:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][c:17]... | CN1CCc2cccc(Nc3cc(Cl)ncc3C#N)c2C1=O.Cc1nn(C)cc1N | Cc1nn(C)cc1Nc1cc(Nc2cccc3c2C(=O)N(C)CC3)c(C#N)cn1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCc2cccc(Nc3ccnc(Nc4cn[nH]c4)c3)c21 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[c:7]1:[#7;a:8]:[#7;a:9](-[C;D1;H3:10]):[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C;D1;H3:6]-[c:7]1:[#7;a:8]:[#7;a:9](-[C;D1;H3:10]):[c:11]:[c:12]:1-[NH;D2;+0:13]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 7.33 | [{"value": 7.33, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C#N)C", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | 6-chloro-4-(2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-8-ylamino)nicotinonitrile (595 mg, 1.90 mmol), Palladium(II) acetate (34.2 mg, 0.15 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (132 mg, 0.23 mmol), 1,3-dimethyl-1H-pyrazol-4-amine (423 mg, 3.80 mmol) and Cesium carbonate (744 mg, 2.28 mmol) were suspe... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1c[nH]nc1.c1ccncc1.c1ccc2c(c1)CC[NH]C2 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CN1CCc2cccc(Nc3cc(Cl)ncc3C#N)c2C1=O.Cc1nn(C)cc1N>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Cc1nn(C)cc1Nc1cc(Nc2cccc3c2C(=O)N(C)CC3)c(C#N)cn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1d37196fb74e494d823157202193321f | CN1CCc2cccc(Nc3cc(Cl)ncc3C#N)c2C1=O.Cc1nn(C)cc1N>>Cc1nn(C)cc1Nc1cc(Nc2cccc3c2C(=O)N(C)CC3)c(C#N)cn1 | CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3C#N)Cl.CC1=NN(C=C1N)C>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C#N)C | Cl[c:9]1[cH:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][c:17]3[c:18]2[C:19](=[O:20])[N:21]([CH3:22])[CH2:23][CH2:24]3)[c:25]([C:26]#[N:27])[cH:28][n:29]1.[CH3:1][c:2]1[n:3][n:4]([CH3:5])[cH:6][c:7]1[NH2:8]>>[CH3:1][c:2]1[n:3][n:4]([CH3:5])[cH:6][c:7]1[NH:8][c:9]1[cH:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][c:17]... | CN1CCc2cccc(Nc3cc(Cl)ncc3C#N)c2C1=O.Cc1nn(C)cc1N | Cc1nn(C)cc1Nc1cc(Nc2cccc3c2C(=O)N(C)CC3)c(C#N)cn1 | C1=CC=C(C=C1)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCc2cccc(Nc3ccnc(Nc4cn[nH]c4)c3)c21 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[c:7]1:[#7;a:8]:[#7;a:9](-[C;D1;H3:10]):[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C;D1;H3:6]-[c:7]1:[#7;a:8]:[#7;a:9](-[C;D1;H3:10]):[c:11]:[c:12]:1-[NH;D2;+0:13]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 54.89 | [{"value": 54.89, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C#N)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | 1,3-dimethyl-1H-pyrazol-4-amine (35.5 mg, 0.32 mmol), 6-chloro-4-(2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-8-ylamino)nicotinonitrile (50 mg, 0.16 mmol)sodium phenolate (18.56 mg, 0.16 mmol),(R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T- BUTYLPHOSPHINE (8.74 mg, 0.02 mmol) and diacetoxypalladium (2.87... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1c[nH]nc1.c1ccncc1.c1ccc2c(c1)CC[NH]C2 | HCl | C1=CC=C(C=C1)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].COCCOC | 150 | null | CN1CCc2cccc(Nc3cc(Cl)ncc3C#N)c2C1=O.Cc1nn(C)cc1N>C1=CC=C(C=C1)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].COCCOC>Cc1nn(C)cc1Nc1cc(Nc2cccc3c2C(=O)N(C)CC3)c(C#N)cn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-13885c2618b74db2ba86072bda25f3e4 | CN1CCc2cccc(Nc3cc(Cl)ncc3C#N)c2C1=O.Cc1nn(C)cc1N>>Cc1nn(C)cc1Nc1cc(Nc2cccc3c2C(=O)N(C)CC3)c(C#N)cn1 | CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3C#N)Cl.CC1=NN(C=C1N)C>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C#N)C | Cl[c:9]1[cH:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][c:17]3[c:18]2[C:19](=[O:20])[N:21]([CH3:22])[CH2:23][CH2:24]3)[c:25]([C:26]#[N:27])[cH:28][n:29]1.[CH3:1][c:2]1[n:3][n:4]([CH3:5])[cH:6][c:7]1[NH2:8]>>[CH3:1][c:2]1[n:3][n:4]([CH3:5])[cH:6][c:7]1[NH:8][c:9]1[cH:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][c:17]... | CN1CCc2cccc(Nc3cc(Cl)ncc3C#N)c2C1=O.Cc1nn(C)cc1N | Cc1nn(C)cc1Nc1cc(Nc2cccc3c2C(=O)N(C)CC3)c(C#N)cn1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCc2cccc(Nc3ccnc(Nc4cn[nH]c4)c3)c21 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[c:7]1:[#7;a:8]:[#7;a:9](-[C;D1;H3:10]):[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C;D1;H3:6]-[c:7]1:[#7;a:8]:[#7;a:9](-[C;D1;H3:10]):[c:11]:[c:12]:1-[NH;D2;+0:13]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 43.75 | [{"value": 43.75, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C#N)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | 1,3-dimethyl-1H-pyrazol-4-amine (355 mg, 3.19 mmol), 6-chloro-4-(2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-8-ylamino)nicotinonitrile (500 mg, 1.60 mmol), Cesium carbonate (625 mg, 1.92 mmol), Palladium(II) acetate (28.7 mg, 0.13 mmol)and (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (87... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1c[nH]nc1.c1ccncc1.c1ccc2c(c1)CC[NH]C2 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].COCCOC | 150 | null | CN1CCc2cccc(Nc3cc(Cl)ncc3C#N)c2C1=O.Cc1nn(C)cc1N>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].COCCOC>Cc1nn(C)cc1Nc1cc(Nc2cccc3c2C(=O)N(C)CC3)c(C#N)cn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b116c54708694e71a57141a571bf1abd | CN1CCc2cccc(Nc3cc(Cl)ncc3C#N)c2C1=O.Cc1nn(C)cc1N>>Cc1nn(C)cc1Nc1cc(Nc2cccc3c2C(=O)N(C)CC3)c(C#N)cn1 | CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3C#N)Cl.CC1=NN(C=C1N)C>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C#N)C | Cl[c:9]1[cH:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][c:17]3[c:18]2[C:19](=[O:20])[N:21]([CH3:22])[CH2:23][CH2:24]3)[c:25]([C:26]#[N:27])[cH:28][n:29]1.[CH3:1][c:2]1[n:3][n:4]([CH3:5])[cH:6][c:7]1[NH2:8]>>[CH3:1][c:2]1[n:3][n:4]([CH3:5])[cH:6][c:7]1[NH:8][c:9]1[cH:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][c:17]... | CN1CCc2cccc(Nc3cc(Cl)ncc3C#N)c2C1=O.Cc1nn(C)cc1N | Cc1nn(C)cc1Nc1cc(Nc2cccc3c2C(=O)N(C)CC3)c(C#N)cn1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCc2cccc(Nc3ccnc(Nc4cn[nH]c4)c3)c21 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[c:7]1:[#7;a:8]:[#7;a:9](-[C;D1;H3:10]):[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C;D1;H3:6]-[c:7]1:[#7;a:8]:[#7;a:9](-[C;D1;H3:10]):[c:11]:[c:12]:1-[NH;D2;+0:13]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 15.63 | [{"value": 15.63, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C#N)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | 6-chloro-4-(2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-8-ylamino)nicotinonitrile (500 mg, 1.60 mmol), 1,3-Dimethyl-1H-pyrazol-4-ylamine (355 mg, 3.20 mmol) and Cesium carbonate (625 mg, 1.92 mmol), Palladium(II) acetate (28.7 mg, 0.13 mmol) and (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t- butylphosph... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1c[nH]nc1.c1ccncc1.c1ccc2c(c1)CC[NH]C2 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].COCCOC | 150 | null | CN1CCc2cccc(Nc3cc(Cl)ncc3C#N)c2C1=O.Cc1nn(C)cc1N>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].COCCOC>Cc1nn(C)cc1Nc1cc(Nc2cccc3c2C(=O)N(C)CC3)c(C#N)cn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1aa2de1a9b014f58b717c720b31e4a66 | Nc1c(Cl)cnc2c1OCO2.O=C(Nc1cc(Cl)ccn1)C1CC1>>O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1 | C1OC2=C(C(=CN=C2O1)Cl)N.C1CC1C(=O)NC2=NC=CC(=C2)Cl>>C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4 | [NH2:7][c:8]1[c:9]([Cl:10])[cH:11][n:12][c:13]2[c:14]1[O:15][CH2:16][O:17]2.Cl[c:6]1[cH:5][c:4]([NH:3][C:2](=[O:1])[CH:21]2[CH2:22][CH2:23]2)[n:20][cH:19][cH:18]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([NH:7][c:8]2[c:9]([Cl:10])[cH:11][n:12][c:13]3[c:14]2[O:15][CH2:16][O:17]3)[cH:18][cH:19][n:20]1)[CH:21]1[CH2:22][CH2:23... | Nc1c(Cl)cnc2c1OCO2.O=C(Nc1cc(Cl)ccn1)C1CC1 | O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1 | C1CCC2=NCCCN2CC1 | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(Nc1cc(Nc2ccnc3c2OCO3)ccn1)C1CC1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]-[C:7]=[O;D1;H0:8]):[c:9]:1.[#8:10]-[c:11]1:[c:12]:[#7;a:13]:[c:14]:[c:15]:[c:16]:1-[NH2;D1;+0:17]>>[#8:10]-[c:11]1:[c:12]:[#7;a:13]:[c:14]:[c:15]:[c:16]:1-[NH;D2;+0:17]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]-[C:7]=[O;D1;H0:8]):[c:9]:1 | 32.5 | [{"value": 32.5, "product": "C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (0.190 mL, 1.27 mmol) was added to a mixture of N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (100 mg, 0.51 mmol), 6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-amine (105 mg, 0.61 mmol) and BIS(DIBENZYLIDENEACETONE)PALLADIUM(0) (26.3 mg, 0.05 mmol) and (9,9-dimethyl-9H-xanthe... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cnc2c(c1)OCO2.C1CC1 | HCl | C1CCC2=NCCCN2CC1.CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].CC1=CC=CC=C1 | 130 | null | Nc1c(Cl)cnc2c1OCO2.O=C(Nc1cc(Cl)ccn1)C1CC1>C1CCC2=NCCCN2CC1.CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].CC1=CC=CC=C1>O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e3d1bf887b8743b5ab0b5887f32d7a64 | Nc1c(Cl)cnc2c1OCO2.O=C(Nc1cc(Cl)ccn1)C1CC1>>O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1 | C1OC2=C(C(=CN=C2O1)Cl)N.C1CC1C(=O)NC2=NC=CC(=C2)Cl>>C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4 | [NH2:7][c:8]1[c:9]([Cl:10])[cH:11][n:12][c:13]2[c:14]1[O:15][CH2:16][O:17]2.Cl[c:6]1[cH:5][c:4]([NH:3][C:2](=[O:1])[CH:21]2[CH2:22][CH2:23]2)[n:20][cH:19][cH:18]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([NH:7][c:8]2[c:9]([Cl:10])[cH:11][n:12][c:13]3[c:14]2[O:15][CH2:16][O:17]3)[cH:18][cH:19][n:20]1)[CH:21]1[CH2:22][CH2:23... | Nc1c(Cl)cnc2c1OCO2.O=C(Nc1cc(Cl)ccn1)C1CC1 | O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(Nc1cc(Nc2ccnc3c2OCO3)ccn1)C1CC1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]-[C:7]=[O;D1;H0:8]):[c:9]:1.[#8:10]-[c:11]1:[c:12]:[#7;a:13]:[c:14]:[c:15]:[c:16]:1-[NH2;D1;+0:17]>>[#8:10]-[c:11]1:[c:12]:[#7;a:13]:[c:14]:[c:15]:[c:16]:1-[NH;D2;+0:17]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]-[C:7]=[O;D1;H0:8]):[c:9]:1 | 32.21 | [{"value": 32.21, "product": "C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (4 g, 20.34 mmol), 6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-amine (3.51 g, 20.34 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.412 g, 2.44 mmol), diacetoxypalladium (0.228 g, 1.02 mmol) and cesium carbonate (13.26 g, 40.68 mmol) were suspended in 1,4-di... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cnc2c(c1)OCO2.C1CC1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 150 | null | Nc1c(Cl)cnc2c1OCO2.O=C(Nc1cc(Cl)ccn1)C1CC1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-53e4c550d2a942e0b2b88b16dae21b0b | Nc1c(Cl)cnc2c1OCO2.O=C(Nc1cc(Cl)ccn1)C1CC1>>O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1 | C1OC2=C(C(=CN=C2O1)Cl)N.C1CC1C(=O)NC2=NC=CC(=C2)Cl>>C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4 | [NH2:7][c:8]1[c:9]([Cl:10])[cH:11][n:12][c:13]2[c:14]1[O:15][CH2:16][O:17]2.Cl[c:6]1[cH:5][c:4]([NH:3][C:2](=[O:1])[CH:21]2[CH2:22][CH2:23]2)[n:20][cH:19][cH:18]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([NH:7][c:8]2[c:9]([Cl:10])[cH:11][n:12][c:13]3[c:14]2[O:15][CH2:16][O:17]3)[cH:18][cH:19][n:20]1)[CH:21]1[CH2:22][CH2:23... | Nc1c(Cl)cnc2c1OCO2.O=C(Nc1cc(Cl)ccn1)C1CC1 | O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(Nc1cc(Nc2ccnc3c2OCO3)ccn1)C1CC1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]-[C:7]=[O;D1;H0:8]):[c:9]:1.[#8:10]-[c:11]1:[c:12]:[#7;a:13]:[c:14]:[c:15]:[c:16]:1-[NH2;D1;+0:17]>>[#8:10]-[c:11]1:[c:12]:[#7;a:13]:[c:14]:[c:15]:[c:16]:1-[NH;D2;+0:17]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]-[C:7]=[O;D1;H0:8]):[c:9]:1 | 28.37 | [{"value": 28.37, "product": "C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (0.8 g, 4.07 mmol), 6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-amine (0.702 g, 4.07 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.282 g, 0.49 mmol), diacetoxypalladium (0.046 g, 0.20 mmol) and cesium carbonate (2.65 g, 8.14 mmol) were suspended in 1,4-dio... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cnc2c(c1)OCO2.C1CC1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 150 | null | Nc1c(Cl)cnc2c1OCO2.O=C(Nc1cc(Cl)ccn1)C1CC1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-97d4ec8781d24990b921a4f59e0aac9e | Nc1c(Cl)cnc2c1OCO2.O=C(Nc1cc(Cl)ccn1)C1CC1>>O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1 | C1OC2=C(C(=CN=C2O1)Cl)N.C1CC1C(=O)NC2=NC=CC(=C2)Cl>>C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4 | [NH2:7][c:8]1[c:9]([Cl:10])[cH:11][n:12][c:13]2[c:14]1[O:15][CH2:16][O:17]2.Cl[c:6]1[cH:5][c:4]([NH:3][C:2](=[O:1])[CH:21]2[CH2:22][CH2:23]2)[n:20][cH:19][cH:18]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([NH:7][c:8]2[c:9]([Cl:10])[cH:11][n:12][c:13]3[c:14]2[O:15][CH2:16][O:17]3)[cH:18][cH:19][n:20]1)[CH:21]1[CH2:22][CH2:23... | Nc1c(Cl)cnc2c1OCO2.O=C(Nc1cc(Cl)ccn1)C1CC1 | O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(Nc1cc(Nc2ccnc3c2OCO3)ccn1)C1CC1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]-[C:7]=[O;D1;H0:8]):[c:9]:1.[#8:10]-[c:11]1:[c:12]:[#7;a:13]:[c:14]:[c:15]:[c:16]:1-[NH2;D1;+0:17]>>[#8:10]-[c:11]1:[c:12]:[#7;a:13]:[c:14]:[c:15]:[c:16]:1-[NH;D2;+0:17]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]-[C:7]=[O;D1;H0:8]):[c:9]:1 | 70.91 | [{"value": 70.91, "product": "C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A mixture of N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (1 g, 5.09 mmol), 6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-amine (0.878 g, 5.09 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.324 g, 0.56 mmol), diacetoxypalladium (0.090 g, 0.40 mmol), cesium carbonate (4.14 g, 12.71 mmol) and dioxane (18 ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cnc2c(c1)OCO2.C1CC1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | Nc1c(Cl)cnc2c1OCO2.O=C(Nc1cc(Cl)ccn1)C1CC1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-43b38b44db094a5e90893913a2fe3478 | Nc1c(Cl)cnc2c1OCO2.O=C(Nc1cc(Cl)ccn1)C1CC1>>O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1 | C1OC2=C(C(=CN=C2O1)Cl)N.C1CC1C(=O)NC2=NC=CC(=C2)Cl>>C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4 | [NH2:7][c:8]1[c:9]([Cl:10])[cH:11][n:12][c:13]2[c:14]1[O:15][CH2:16][O:17]2.Cl[c:6]1[cH:5][c:4]([NH:3][C:2](=[O:1])[CH:21]2[CH2:22][CH2:23]2)[n:20][cH:19][cH:18]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([NH:7][c:8]2[c:9]([Cl:10])[cH:11][n:12][c:13]3[c:14]2[O:15][CH2:16][O:17]3)[cH:18][cH:19][n:20]1)[CH:21]1[CH2:22][CH2:23... | Nc1c(Cl)cnc2c1OCO2.O=C(Nc1cc(Cl)ccn1)C1CC1 | O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(Nc1cc(Nc2ccnc3c2OCO3)ccn1)C1CC1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]-[C:7]=[O;D1;H0:8]):[c:9]:1.[#8:10]-[c:11]1:[c:12]:[#7;a:13]:[c:14]:[c:15]:[c:16]:1-[NH2;D1;+0:17]>>[#8:10]-[c:11]1:[c:12]:[#7;a:13]:[c:14]:[c:15]:[c:16]:1-[NH;D2;+0:17]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]-[C:7]=[O;D1;H0:8]):[c:9]:1 | 43.73 | [{"value": 43.73, "product": "C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (0.8 g, 4.07 mmol), 6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-amine (0.702 g, 4.07 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.282 g, 0.49 mmol), diacetoxypalladium (0.046 g, 0.20 mmol) and cesium carbonate (2.65 g, 8.14 mmol) were suspended in 1,4-dio... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cnc2c(c1)OCO2.C1CC1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 150 | null | Nc1c(Cl)cnc2c1OCO2.O=C(Nc1cc(Cl)ccn1)C1CC1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-69adc3b86d5e4e688ca79adbe7928bc5 | CCN1CCNCC1.O=c1cc(N2CCOCC2)oc2c(-c3ccc(I)c4c3sc3ccccc34)cccc12>>CCN1CCN(c2ccc(-c3cccc4c(=O)cc(N5CCOCC5)oc34)c3sc4ccccc4c23)CC1 | C1COCCN1C2=CC(=O)C3=C(O2)C(=CC=C3)C4=C5C(=C(C=C4)I)C6=CC=CC=C6S5.CCN1CCNCC1>>CCN1CCN(CC1)C2=C3C4=CC=CC=C4SC3=C(C=C2)C5=CC=CC6=C5OC(=CC6=O)N7CCOCC7 | [CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][NH:6][CH2:37][CH2:38]1.I[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]3[c:16](=[O:17])[cH:18][c:19]([N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)[o:26][c:27]23)[c:28]2[s:29][c:30]3[cH:31][cH:32][cH:33][cH:34][c:35]3[c:36]12>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7... | CCN1CCNCC1.O=c1cc(N2CCOCC2)oc2c(-c3ccc(I)c4c3sc3ccccc34)cccc12 | CCN1CCN(c2ccc(-c3cccc4c(=O)cc(N5CCOCC5)oc34)c3sc4ccccc4c23)CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | f7a393ea76d0a69902b50309971dec516c000f77be9559e495f502535b7d1ca4 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(-c3ccc(N4CCNCC4)c4c3sc3ccccc34)cccc12 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#16;a:6]:[c:7]:[c:8]:[c:9]:2:1.[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[#16;a:6]1:[c:7]:[c:8]:[c:9]2:[c:5]:1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:2-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-1 | 48.74 | [{"value": 48.74, "product": "CCN1CCN(CC1)C2=C3C4=CC=CC=C4SC3=C(C=C2)C5=CC=CC6=C5OC(=CC6=O)N7CCOCC7", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | 8-(1-iododibenzo[b,d]thiophen-4-yl)-2-morpholino-4H-chromen-4-one (2 g, 3.71 mmol), 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (0.462 g, 0.74 mmol), CESIUM CARBONATE (3.62 g, 11.12 mmol) and PALLADIUM (II) ACETATE (0.166 g, 0.74 mmol) were weighed out in a flask and inerted with argon. toluene (25 ml) and 1-ethylpiper... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccc2c(c1)sc1ccccc12 | C1C[NH]CC[NH]1.c1ccc2c(c1)sc1ccccc12 | C1C[NH]CC[NH]1.c1ccc2ccccc2o1.C1COCC[NH]1.c1ccc2c(c1)sc1ccccc12 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 110 | null | CCN1CCNCC1.O=c1cc(N2CCOCC2)oc2c(-c3ccc(I)c4c3sc3ccccc34)cccc12>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CCN1CCN(c2ccc(-c3cccc4c(=O)cc(N5CCOCC5)oc34)c3sc4ccccc4c23)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8dc05311ad5340e693477414d5741a5e | CCN1CCNCC1.O=c1cc(N2CCOCC2)oc2c(-c3ccc(I)c4c3sc3ccccc34)cccc12>>CCN1CCN(c2ccc(-c3cccc4c(=O)cc(N5CCOCC5)oc34)c3sc4ccccc4c23)CC1 | C1COCCN1C2=CC(=O)C3=C(O2)C(=CC=C3)C4=C5C(=C(C=C4)I)C6=CC=CC=C6S5.CCN1CCNCC1>>CCN1CCN(CC1)C2=C3C4=CC=CC=C4SC3=C(C=C2)C5=CC=CC6=C5OC(=CC6=O)N7CCOCC7 | [CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][NH:6][CH2:37][CH2:38]1.I[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]3[c:16](=[O:17])[cH:18][c:19]([N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)[o:26][c:27]23)[c:28]2[s:29][c:30]3[cH:31][cH:32][cH:33][cH:34][c:35]3[c:36]12>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7... | CCN1CCNCC1.O=c1cc(N2CCOCC2)oc2c(-c3ccc(I)c4c3sc3ccccc34)cccc12 | CCN1CCN(c2ccc(-c3cccc4c(=O)cc(N5CCOCC5)oc34)c3sc4ccccc4c23)CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | f7a393ea76d0a69902b50309971dec516c000f77be9559e495f502535b7d1ca4 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(-c3ccc(N4CCNCC4)c4c3sc3ccccc34)cccc12 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#16;a:6]:[c:7]:[c:8]:[c:9]:2:1.[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[#16;a:6]1:[c:7]:[c:8]:[c:9]2:[c:5]:1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:2-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-1 | 0 | [{"value": 0.0, "product": "CCN1CCN(CC1)C2=C3C4=CC=CC=C4SC3=C(C=C2)C5=CC=CC6=C5OC(=CC6=O)N7CCOCC7", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | 8-(1-iododibenzo[b,d]thiophen-4-yl)-2-morpholino-4H-chromen-4-one (20 mg, 0.04 mmol), 1-ethylpiperazine (9.42 µl, 0.07 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.145 mg, 3.71 µmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (0.849 mg, 0.93 µmol) and 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccc2c(c1)sc1ccccc12 | C1C[NH]CC[NH]1.c1ccc2c(c1)sc1ccccc12 | C1C[NH]CC[NH]1.c1ccc2ccccc2o1.C1COCC[NH]1.c1ccc2c(c1)sc1ccccc12 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 130 | null | CCN1CCNCC1.O=c1cc(N2CCOCC2)oc2c(-c3ccc(I)c4c3sc3ccccc34)cccc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCN1C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8b6e9d49ac804667b43344fcaf4ab862 | CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-]>>COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-] | COC1=C(C=C(C=C1)Br)[N+](=O)[O-].CC(=O)N1CCNCC1>>CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-] | [NH:7]1[CH2:8][CH2:9][N:10]([C:11]([CH3:12])=[O:13])[CH2:14][CH2:15]1.Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:17]([N+:18](=[O:19])[O-:20])[cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11]([CH3:12])=[O:13])[CH2:14][CH2:15]2)[cH:16][c:17]1[N+:18](=[O:19])[O-:20] | CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-] | COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-] | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 29.91 | [{"value": 29.91, "product": "CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-]", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 4-bromo-1-methoxy-2-nitrobenzene (30 g, 129.29 mmol), 1-(piperazin-1-yl)ethanone (16.57 g, 129.29 mmol), cesium carbonate (84 g, 258.59 mmol),diacetoxypalladium (2.322 g, 10.34 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (8.98 g, 15.52 mmol) in dioxane (200 mL) were degazed with nitrogen and st... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-]>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-] |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7efc5b9774d04fb09dba803fb4f7b480 | CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-]>>COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-] | COC1=C(C=C(C=C1)Br)[N+](=O)[O-].CC(=O)N1CCNCC1>>CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-] | [NH:7]1[CH2:8][CH2:9][N:10]([C:11]([CH3:12])=[O:13])[CH2:14][CH2:15]1.Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:17]([N+:18](=[O:19])[O-:20])[cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11]([CH3:12])=[O:13])[CH2:14][CH2:15]2)[cH:16][c:17]1[N+:18](=[O:19])[O-:20] | CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-] | COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-] | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 82.89 | [{"value": 82.89, "product": "CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-]", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | 1-(piperazin-1-yl)ethanone (9.94 g, 77.58 mmol), Cesium carbonate (50.6 g, 155.15 mmol), XANTPHOS (5.39 g, 9.31 mmol) and Pd(OAc)2 (1.393 g, 6.21 mmol) were added to a stirred solution of 4-bromo-1-methoxy-2-nitrobenzene (18 g, 77.58 mmol) dissolved in dioxane (120 ml). The resulting suspension was heated to 120 °C (ba... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 120 | null | CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-]>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-] |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-56a1dc90e93f4e37a4c4dceba5d45c4e | CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-]>>COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-] | COC1=C(C=C(C=C1)Br)[N+](=O)[O-].CC(=O)N1CCNCC1>>CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-] | [NH:7]1[CH2:8][CH2:9][N:10]([C:11]([CH3:12])=[O:13])[CH2:14][CH2:15]1.Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:17]([N+:18](=[O:19])[O-:20])[cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11]([CH3:12])=[O:13])[CH2:14][CH2:15]2)[cH:16][c:17]1[N+:18](=[O:19])[O-:20] | CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-] | COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-] | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 1.22 | [{"value": 1.22, "product": "CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-]", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | 4-bromo-1-methoxy-2-nitrobenzene (1.5 g, 6.46 mmol), 1-(piperazin-1-yl)ethanone (0.829 g, 6.46 mmol), CESIUM CARBONATE (4.21 g, 12.93 mmol), XANTPHOS (0.449 g, 0.78 mmol) and PdOAc2 (0.116 g, 0.52 mmol) were suspended in dioxane (20 ml) and sealed into a microwave tube. The reaction was heated to 120 °C for 90 minutes ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 120 | null | CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-]>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-] |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-05f07a62b42e4c23af01e32b4f5a3985 | CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-]>>COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-] | COC1=C(C=C(C=C1)Br)[N+](=O)[O-].CC(=O)N1CCNCC1>>CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-] | [NH:7]1[CH2:8][CH2:9][N:10]([C:11]([CH3:12])=[O:13])[CH2:14][CH2:15]1.Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:17]([N+:18](=[O:19])[O-:20])[cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11]([CH3:12])=[O:13])[CH2:14][CH2:15]2)[cH:16][c:17]1[N+:18](=[O:19])[O-:20] | CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-] | COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-] | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 1.38 | [{"value": 1.38, "product": "CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-]", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | 4-bromo-1-methoxy-2-nitrobenzene (1.5 g, 6.46 mmol) was added in one portion to 1-(piperazin-1-yl)ethanone (0.829 g, 6.46 mmol), CESIUM CARBONATE (4.21 g, 12.93 mmol), XANTPHOS (0.449 g, 0.78 mmol) and PdOAc2 (0.116 g, 0.52 mmol) in dioxane (20 ml) under nitrogen. The resulting mixture was stirred at 120 °C for 3 hours... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 120 | null | CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-]>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-] |
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