Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [CH3:1][CH:2]([CH3:30])[CH:3]([N:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[C:10]1=[O:29])[C:4]([O:6]CC)=[O:5].[OH-].[Na+]>CO>[CH3:1][CH:2]([CH3:30])[CH:3]([N:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[C:10]1=[O:29])[C:4]([OH:6])=[O:5]
Reactant: CCOC(=O)C(C(C)C)N1CCN(Cc2ccc(OCc3ccncc3)cc2)C1=O
Agent: [Na+]
Agent: [OH-]
Solvent: CO
Product: CC(C)C(C(=O)O)N1CCN(Cc2ccc(OCc3ccncc3)cc2)C1=O
Temperature: 0 °C
Yield: 81.8 %

Procedure:
Ethyl 3-methyl-2-{2-oxo-3-(4-(pyridin-4-ylmethoxy)benzyl)imidazolidin-1-yl}-butyrate (45 mg; 0.11 mmol) was dissolved in methanol (1.5 ml) and cooled to 0° C. NaOH (1N, 5 ml) was added, and the mixture was allowed to warm to RT over the course of 3 h. The methanol was then removed under reduced pressure, and water (1.5 ml) and saturated NaH2PO4 solution (3 ml) were added to the residue. The solid was filtered off with suction and washed with water. Drying under reduced pressure at 60° C. resulted in 3-methyl-2-{2-oxo-3-(4-(pyridin-4-ylmethoxy)benzyl)imidazolidin-1-yl}-butyric acid (36 mg; 0.09 mmol). MS: 384.45 (M+H); Rt: 0.87 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)
Reaction SMILES: C([O:3][C:4]1[CH2:13][C:12]2[C:11]([NH:14][C:15]3[O:16][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[CH3:26])=[CH:18][N:19]=3)=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH:5]=1)C.C(OC1CC2C(NC3OC(C4C=CC(C(F)(F)F)=CC=4)=CN=3)=CC=CC=2CC=1)C>>[CH3:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:17]1[O:16][C:15]([NH:14][C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:12]=2[CH2:13][C:4](=[O:3])[CH2:5][CH2:6]3)=[N:19][CH:18]=1
Reactant: CCOC1=CCc2cccc(Nc3ncc(-c4ccccc4C)o3)c2C1
Agent: CCOC1=CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1
Product: Cc1ccccc1-c1cnc(Nc2cccc3c2CC(=O)CC3)o1

Procedure:
The title compound was prepared using the procedure as described in Example 1I, substituting the product of Example 14B for the product of Example 1H.
Reaction SMILES: N[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5](O)=[CH:4][CH:3]=1.C(N=C=O)(C)=C>C(Cl)(Cl)Cl>[CH:9]1[C:8]2[C:7](=[O:17])[C:6]3[C:15](=[CH:2][CH:3]=[CH:4][CH:5]=3)[C:14](=[O:16])[C:13]=2[CH:12]=[CH:11][CH:10]=1
Reactant: Nc1ccc(O)c2c1C(=O)c1ccccc1C2=O
Agent: C=C(C)N=C=O
Solvent: ClC(Cl)Cl
Product: O=C1c2ccccc2C(=O)c2ccccc21

Procedure:
A solution prepared by adding 0.005 part of methoquinone to 24 parts of 1-amino-4-hydroxy-anthraquinone and dissolving the obtained mixture in 900 parts of dried chloroform was cooled with ice in a nitrogen atmosphere. Then, 18 parts of isopropenyl isocyanate was dropped into the resulting solution. After the completion of the dropping, the obtained mixture was stirred under cooling with ice for 3 hours to complete a reaction. Then, the obtained reaction mixture was freed from the chloroform by distillation and recrystallized from ethanol to give a yellow polymerizable anthraquinone dye E. The anthraquinone dye E is represented by the below chemical formula (VI). ##STR6##
Reaction SMILES: [O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[NH:8][C:7]([C:14]3[CH:24]=[CH:23][C:17](/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21])=[CH:16][CH:15]=3)=[N:6][C:5]=2[C:4](=[O:25])[N:3]1[CH2:26][CH2:27][CH3:28].S(=O)(=O)(O)O.[CH2:34](O)[CH3:35]>>[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[NH:8][C:7]([C:14]3[CH:24]=[CH:23][C:17](/[CH:18]=[CH:19]/[C:20]([O:22][CH2:34][CH3:35])=[O:21])=[CH:16][CH:15]=3)=[N:6][C:5]=2[C:4](=[O:25])[N:3]1[CH2:26][CH2:27][CH3:28]
Reactant: CCCn1c(=O)c2nc(-c3ccc(/C=C/C(=O)O)cc3)[nH]c2n(CCC)c1=O
Reactant: CCO
Agent: O=S(=O)(O)O
Product: CCCn1c(=O)c2nc(-c3ccc(/C=C/C(=O)OCC)cc3)[nH]c2n(CCC)c1=O
Reaction time: 72 h

Procedure:
A suspension of (E)-4-(1,2,3,6-tetrahydro-2,6-dioxo-1,3-dipropyl-9H-purin-8-yl)cinnamic acid (4.00 g, 10.4 mmol) (Example 6) and concentrated sulfuric acid (1 ml) in absolute ethanol (1.5 L) was refluxed for 2 hours with slow distillation of 75 ml of vapor. Reflux was continued for 3 days with exclusion of moisture with 50 ml distillate being removed during the final 4 hours. The cooled suspension was filtered to yield ethyl (E)-4-(1,2,3,6-tetrahydro-2,6-dioxo-1,3-dipropyl-9H-purin-8-yl)cinnamate as a pale yellow solid. mp >300° C. Analysis for (C22H26N4O4). C, 64.38; H, 6.38; N, 13.65. Found: C, 64.34; H, 6.43; N, 13.63.
Reaction SMILES: [CH2:1]([O:4][C:5]1[C:10]([N+:11]([O-])=O)=[CH:9][C:8]([Br:14])=[CH:7][C:6]=1[F:15])[CH:2]=[CH2:3].O.O.[Sn](Cl)(Cl)(Cl)Cl.C(N(CC)CC)C>C(O)C>[CH2:1]([O:4][C:5]1[C:6]([F:15])=[CH:7][C:8]([Br:14])=[CH:9][C:10]=1[NH2:11])[CH:2]=[CH2:3]
Reactant: C=CCOc1c(F)cc(Br)cc1[N+](=O)[O-]
Agent: Cl[Sn](Cl)(Cl)Cl
Solvent: CCN(CC)CC
Solvent: CCO
Solvent: O
Product: C=CCOc1c(N)cc(Br)cc1F
Yield: 55 %

Procedure:
A mixture of Example 89A (1.3 g, 4.71 mmol), tin chloride dihydrate (5.3 g, 23.5 mmol) and triethylamine (13.1 mL, 94.2 mmol) in ethanol (50 mL) was heated at 70° C. for 6 hours, cooled. The insoluble material was filtered off and extensively washed with ethyl acetate. The combined filtrate was concentrated, and the residue was purified by flash chromatography eluting with 5% ethyl acetate in dichloromethane to provide the desired product (638 mg, 55%). MS (DCI/NH3) m/z 247.82 (M+H)+; 1H NMR (500 MHz, DMSO-D6) δ ppm 4.41 (d, J=5.93 Hz, 2 H) 5.20 (dd, J=10.45, 1.72 Hz, 1 H) 5.30 (dd, J=17.31, 1.72 Hz, 1 H) 5.43 (s, 2 H) 6.03 (m, 1 H) 6.56 (dd, J=10.29, 2.50 Hz, 1 H) 6.66 (dd, J=2.34, 1.72 Hz, 1 H).
Reaction SMILES: [OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Br[CH2:37][CH:38]([CH3:40])[CH3:39]>CCOC(C)=O>[CH3:37][CH:38]([CH3:40])[CH2:39][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[N:9]=2)=[CH:4][CH:3]=1
Reactant: CC(C)CBr
Reactant: N#Cc1ccc2c(c1)c(-c1ccc(O)cc1)nn2C1CCCCO1
Agent: O=C([O-])[O-]
Agent: [K+]
Solvent: CCOC(C)=O
Solvent: CN(C)C=O
Product: CC(C)COc1ccc(-c2nn(C3CCCCO3)c3ccc(C#N)cc23)cc1
Temperature: 25 °C
Reaction time: 2 h
Yield: 73.8 %

Procedure:
A mixture of 3-(4-hydroxyphenyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (219 mg, 0.686 mmol), potassium carbonate (K2CO3, 568 mg, 4.12 mmol, 6.00 equiv.), 2.00 mL of dimethylformamide (DMF), and 1-bromo-2-methylpropane (Aldrich, 300 mg, 2.18 mmol, 3.20 equiv.) were stirred at room temperature for 2 h, and then heated at 40° C. for 22 h. Additional potassium carbonate (568 mg, 4.12 mmol, 6.00 equiv.), and 1-bromo-2-methylpropane (Aldrich, 300 mg, 2.18 mmol, 3.20 equiv.) were added, and heating continued for another 28 h. The mixture was diluted with EtOAc, washed with 2× sat. aq. NaHCO3, 2× sat. aq. NaCl, and dried (Na2SO4). Purification by silica gel chromatography using 20% EtOAc in hexanes afforded the title compound (190 mg, 73.6% yield): ES-MS (m/z) 376 [M+1]+.
Reaction SMILES: [OH:1][C@@H:2]([CH2:6][CH:7]1[CH2:9][CH2:8]1)[C:3]([OH:5])=[O:4].[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1>CN(C=O)C>[OH:1][C@@H:2]([CH2:6][CH:7]1[CH2:9][CH2:8]1)[C:3]([O:5][CH2:16][C:15]1[CH:18]=[CH:19][C:12]([O:11][CH3:10])=[CH:13][CH:14]=1)=[O:4]
Reactant: COc1ccc(CCl)cc1
Reactant: O=C(O)[C@@H](O)CC1CC1
Solvent: CN(C)C=O
Product: COc1ccc(COC(=O)[C@@H](O)CC2CC2)cc1

Procedure:
A solution of 4.30 g (33 mmol) of 2-(S)-hydroxy-3-(cyclopropyl)propanoic acid (from Step A), 6.40 mL (46 mmol) of TEA and 5.90 mL (44 mmol) of 4-(methoxy)benzyl chloride in 40 mL of DMF was stirred at rt for 2 h. The mixture was partitioned between 500 mL of ether and 300 mL of H2O and the layers were separated. The organic layer was washed with 300 mL of 2.0 N HCl, 300 mL of sat'd NaHCO3, 2×300 mL of H2O, 300 mL of sat'd NaCl, dried over MgSO4 and concentrated. Flash chromatography on 500 g of silica gel using 5:1 v/v hexanes/EtOAc as the eluant afforded 4.30 g (52%, 97.5% ee) of the title compound: RF: 0.20 (4:1 v/v hexanes/EtOAc); 1H NMR (300 MHz): δ 0.01-0.09 (m, 2H), 0.40-0.45 (m, 2H), 0.84 (m, 1H), 1.55-1.67 (m, 2H), 2.82 (br m, 1H), 3.81 (s, 3H), 4.25 (br m, 1H), 5.14 (ABq, J=11.8, 2H), 6.90 (d, J=8.7, 2H), 7.29 (d, J=8.7, 2H). HPLC: Chiracel OB 4.6×250 mm column, 65:35 v/v hexanes/EtOH, 0.5 mL/min, 220 nm. Retention times: (S)-enantiomer, 20.4 min; (R)-enantiomer, 17.3 min.