Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[CH2:23][CH2:24][C:25](O)=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([N:35]1[CH2:40][CH2:39][N:38]([C:41](=[O:56])[C@H:42]([CH2:51][CH2:52][C:53](=[O:55])[NH2:54])[NH:43]C(OC(C)(C)C)=O)[CH2:37][CH2:36]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=[CH:11][C:10]=1[CH2:23][CH2:24][C:25]([NH:43][C@H:42]([C:41]([N:38]1[CH2:37][CH2:36][N:35]([CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:40][CH2:39]1)=[O:56])[CH2:51][CH2:52][C:53](=[O:55])[NH2:54])=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
Reactant: CC(C)(C)OC(=O)N[C@@H](CCC(N)=O)C(=O)N1CCN(Cc2ccccc2)CC1
Reactant: O=C(O)CCc1ccc(OCc2ccccc2)cc1OCc1ccccc1
Product: NC(=O)CC[C@H](NC(=O)CCc1ccc(OCc2ccccc2)cc1OCc1ccccc1)C(=O)N1CCN(Cc2ccccc2)CC1
Yield: 89.6 %

Procedure:
Condensation of 3-(2,4-dibenzyloxyphenyl) propionic acid (748 mg) and 1-benzyl-4-(N-tert-butoxycarbonyl-L-glutaminyl)piperazine (1.0 g) was effected in the same manner as in Example 8 (i) to obtain colorless crystalline powder 1-[3-(2,4-dibenzyloxyphenyl)propionyl-L-glutaminyl]-4-benzylpiperazine (1.20 g). Melting point: 145°-147° C.
Reaction SMILES: [NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([NH:10][C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:7][C:6]=2[CH:19]=1.Cl[C:21]1[C:30]2[C:25](=[CH:26][C:27]([O:42][CH3:43])=[C:28]([O:31][CH2:32][CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]3)[CH:29]=2)[N:24]=[CH:23][N:22]=1.Cl.O1CCOCC1>C(O)CCC>[CH3:43][O:42][C:27]1[CH:26]=[C:25]2[C:30]([C:21]([NH:1][C:2]3[CH:3]=[CH:4][C:5]4[S:9][C:8]([NH:10][C:11](=[O:18])[C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=5)=[N:7][C:6]=4[CH:19]=3)=[N:22][CH:23]=[N:24]2)=[CH:29][C:28]=1[O:31][CH2:32][CH2:33][CH2:34][N:35]1[CH2:36][CH2:37][N:38]([CH3:41])[CH2:39][CH2:40]1
Reactant: COc1cc2ncnc(Cl)c2cc1OCCCN1CCN(C)CC1
Reactant: Nc1ccc2sc(NC(=O)c3ccccc3)nc2c1
Agent: Cl
Solvent: CCCCO
Solvent: C1COCCO1
Product: COc1cc2ncnc(Nc3ccc4sc(NC(=O)c5ccccc5)nc4c3)c2cc1OCCCN1CCN(C)CC1

Procedure:
N-(5-{7-Methoxy-6-[3-(4-methyl-piperazin-1-yl)-propoxy]-quinazolin-4-ylamino}-benzothiazol-2-yl)-benzamide was prepared by heating a mixture of N-(5-aminobenzothiazol-2-yl)benzamide (IM 5, 35 mg, 0.13 mmol), 4-chloro-7-methoxy-6-[3-(4-methylpiperazin-1-yl)propoxy]quinazoline (IM 8, 46 mg, 0.13 mmol) and 4 M HCl in dioxane (0.09 mL, 0.39 mmol) in n-butanol (3 mL) to 110° C. for 5 h. The HCl salt of the product precipitated. It was separated by filtration and washed twice with CH2Cl2. No ether purification was necessary (65 mg, 0.1 mmol, 93%). LC:/ESI-MS: m/z=620 [M+H]+; m/z=618 [M−H]−; Rt=2.43 min.
Reaction SMILES: C(Cl)(Cl)(Cl)Cl.O.[CH2:7]([O:14][CH2:15][C@H:16]1[O:18][C@H:17]1[CH2:19][OH:20])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C[CH2:22][O:23]CC>>[CH2:7]([O:14][CH2:15][C@H:16]1[O:18][C@H:17]1[C:19]([O:23][CH3:22])=[O:20])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
Reactant: CCOCC
Reactant: OC[C@@H]1O[C@@H]1COCc1ccccc1
Solvent: O
Solvent: ClC(Cl)(Cl)Cl
Product: COC(=O)[C@@H]1O[C@@H]1COCc1ccccc1
Temperature: 0 °C
Reaction time: 2 h

Procedure:
To a solution of 10 ml CCl4, 10 ml CH3CH, and 15 ml of H2O was added 50 mg of RuCl3 --H2O and 1.00 g (5.16 mmole) of (2S-cis)-3-(benzyloxymethyl)oxirane methanol. The solution was cooled to 0° C. and 3.50 g (15.5 mmole) of H5IO6 was added in portions over 15 min with vigorous stirring. The reaction was allowed to stir vigorously for 2 hours. The mixture was poured into 100 ml of Et2O, the organic layer separated and the aqueous layer washed with 20 ml of Et2O. The combined organic layers were washed four times with 50 ml 0.1 N NaOH. The aqueous layers were combined, acidified to pH 2, and extracted three times with 50 ml Et2O. The ether layers were dried over MgSO4, filtered and evaporated to yield a pale yellow residue.
Reaction SMILES: [C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]=3[O:29][C:30]3[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-]#N.[Na+].[CH3:41][OH:42]>C(Cl)Cl.CCOC(C)=O.O=[Mn]=O>[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[C:24]([C:25]([F:27])([F:26])[F:28])=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]=3[O:29][C:30]3[CH:31]=[CH:32][C:33]([C:34]([O:42][CH3:41])=[O:35])=[CH:36][CH:37]=3)=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
Reactant: CO
Reactant: O=Cc1ccc(Oc2c(-c3ccc(OCc4ccccc4)cc3)c(C(F)(F)F)cc3ccccc23)cc1
Agent: O=[Mn]=O
Agent: [C-]#N
Agent: [Na+]
Solvent: ClCCl
Solvent: CCOC(C)=O
Product: COC(=O)c1ccc(Oc2c(-c3ccc(OCc4ccccc4)cc3)c(C(F)(F)F)cc3ccccc23)cc1
Temperature: 25 °C
Reaction time: 8 h
Yield: 86 %

Procedure:
To a solution of 4-{[2-{4-[(phenylmethyl)oxy]phenyl}-3-(trifluoromethyl)-1-naphthalenyl]oxy}benzaldehyde (187) (0.23 g, 0.45 mmol) in MeOH (4 mL) and CH2Cl2 (2 mL) was added NaCN (0.12 g, 2.26 mmol) followed by MnO2 (0.56 g, 5.42 mmol). The reaction mixture was stirred at room temperature overnight, diluted with EtOAc (50 mL) and filtered through a pad of celite on top of a layer of silica gel. The filtrate was washed with water, brine, dried over Na2SO4, filtered, and concentrated to give the crude product as a light yellow solid, which upon trituration with 1% MeOH in hexanes, gave 0.21 g (86%) of the title compound (188) as a white solid. mp 131-132° C. 1H NMR (400 MHz, CDCl3): δ 3.85 (s, 3H), 5.01 (s, 2H), 6.58 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.6 Hz, 2H), 7.05 (d, J=8.6 Hz, 2H), 7.30-7.44 (m, 5H), 7.55-7.66 (m, 2H), 7.79 (d, J=8.8 Hz, 2H), 7.89 (d, J=8.2 Hz, 1H), 8.03 (d, J=8.1 Hz, 1H), 8.24 (s, 1H). LCMS (ESI): m/z 551 (M+Na)+.
Reaction SMILES: [C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:16]3=[O:26])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].[N+:27]([O-])([OH:29])=[O:28]>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:11][C:12]([N:15]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:16]3=[O:26])=[C:13]([N+:27]([O-:29])=[O:28])[CH:14]=2)=[CH:7][CH:8]=1)#[N:2]
Reactant: O=[N+]([O-])O
Reactant: COC(=O)CCN1CCN(c2ccc(-c3ccc(C#N)cc3)cc2)C1=O
Product: COC(=O)CCN1CCN(c2ccc(-c3ccc(C#N)cc3)cc2[N+](=O)[O-])C1=O

Procedure:
Prepared by reacting 1-(4'-cyano-4-biphenylyl)-3-(2-methoxycarbonyl-ethyl)-imidazolidin-2-one with fuming nitric acid at 0° C.
Reaction SMILES: [F:1][C:2]([F:33])([F:32])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3[CH:14]=[CH:15][C:16]([O:18][C:19]4[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=4)[O:22][CH:23]([CH2:27][CH3:28])[C:24]([OH:26])=[O:25])=[CH:17][C:12]=3[O:11][N:10]=2)=[CH:5][CH:4]=1.[B-](F)(F)(F)[F:35].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C>[F:35][C:20]1[C:19]([O:18][C:16]2[CH:15]=[CH:14][C:13]3[C:9]([C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:32])[F:33])=[CH:8][CH:7]=4)=[N:10][O:11][C:12]=3[CH:17]=2)=[CH:31][CH:30]=[CH:29][C:21]=1[O:22][CH:23]([CH2:27][CH3:28])[C:24]([OH:26])=[O:25]
Reactant: F[B-](F)(F)F
Reactant: CCC(Oc1cccc(Oc2ccc3c(-c4ccc(C(F)(F)F)cc4)noc3c2)c1)C(=O)O
Agent: F[N+]12CC[N+](CCl)(CC1)CC2
Solvent: CC#N
Product: CCC(Oc1cccc(Oc2ccc3c(-c4ccc(C(F)(F)F)cc4)noc3c2)c1F)C(=O)O

Procedure:
A solution of the title compound of example 10 (92 mg, 0.2 mmol) and SELECTFLUOR™ (Aldrich, 70 mg, 0.2 mmol) in acetonitrile (2.0 mL) was heated at 60° C. for 16 hrs. The reaction mixture was directly purified by preparative HPLC on a 100×20 mm YMC C-18 column using 0.1% TFA modified CH3CN—H2O solvent system as the eluent to afford the title compound.