Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:19][C:18]3[C:13](=[N:14][C:15]([C:20]([OH:22])=O)=[CH:16][CH:17]=3)[C:12]=2[NH:23][C:24]([C@H:26]2[CH2:31][CH2:30][C@H:29]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][C:33]3=[O:38])[CH2:28][CH2:27]2)=[O:25])=[O:10])=[N:6][CH:7]=1.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C.O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:19][C:18]3[C:13](=[N:14][C:15]([C:20]([N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)=[O:22])=[CH:16][CH:17]=3)[C:12]=2[NH:23][C:24]([C@H:26]2[CH2:27][CH2:28][C@H:29]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][C:33]3=[O:38])[CH2:30][CH2:31]2)=[O:25])=[O:10])=[N:6][CH:7]=1
Reactant: C1COCCN1
Reactant: O=C(O)c1ccc2oc(C(=O)Nc3ccc(Cl)cn3)c(NC(=O)[C@H]3CC[C@H](N4CCOCC4=O)CC3)c2n1
Agent: CCN=C=NCCCN(C)C
Agent: Cl
Agent: On1nnc2ccccc21
Solvent: CN(C)C=O
Solvent: CCOC(C)=O
Solvent: C1CCOC1
Product: O=C(Nc1ccc(Cl)cn1)c1oc2ccc(C(=O)N3CCOCC3)nc2c1NC(=O)[C@H]1CC[C@H](N2CCOCC2=O)CC1
Temperature: 25 °C
Reaction time: 15 h

Procedure:
2-{[(5-Chloropyridin-2-yl)amino]carbonyl}-3-({[trans-4-(3-oxomorpholin-4-yl)cyclohexyl]carbonyl}amino)furo[3,2-b]pyridine-5-carboxylic acid (100 mg) obtained in Example 79 is dissolved in N,N-dimethylformamide (3 ml), and thereto are added successively morpholine (32 μl), 1-hydroxybenzotriazole (50 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (71 mg), and the mixture is stirred at room temperature for 15 hours. The reaction solution is diluted with ethyl acetate-tetrahydrofuran, and the solution is washed successively with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over sodium sulfate. The solvent is evaporated under reduced pressure and the resulting residue is suspended in ethyl acetate-diethyl ether. The solid precipitates are collected by filtration to give the title compound (109 mg).
Reaction SMILES: Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[NH2:12][C:13]1[S:14][CH:15]=[C:16]([CH3:18])[N:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[CH3:18][C:16]1[N:17]=[C:13]([NH:12][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=2)[C:5]([O:7][CH3:8])=[O:6])[S:14][CH:15]=1
Reactant: COC(=O)c1ccnc(Cl)c1
Reactant: Cc1csc(N)n1
Agent: [Pd]
Agent: CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21
Agent: O=C(/C=C/c1ccccc1)/C=C/c1ccccc1
Solvent: Cc1ccccc1
Solvent: O
Product: COC(=O)c1ccnc(Nc2nc(C)cs2)c1
Yield: 71.5 %

Procedure:
Using the method of Example 3, Step B, 2-chloroisonicotinic acid, methyl ester (4.734 g, 27.59 mmol), 2-amino-4-methylthiazole (3.0 g, 26.28 mmol), potassium phosphate (2.393 ml, 28.90 mmol), Pd2(dba)3 (0.6016 g, 0.6569 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.4181 g, 0.7226 mmol) in toluene (20 mL) and water (0.5 mL) were reacted to afford methyl 2-(4-methylthiazol-2-ylamino)isonicotinate (4.682 g, 71.48% yield) as a white solid. 1H NMR (CDCl3) δ 10.25 (bs, 1H), 8.47 (dd, 1H), 7.40 (m, 1H), 7.39 (dd, 1H), 6.45 (d, 1H), 3.94 (s, 3H), 2.39 (d, 3H); Mass spectrum (apci) m/z=250 (100) (M+H).
Reaction SMILES: [Br:1][C:2]1[CH:7]=[C:6]2[NH:8][CH2:9][C:10]3([CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.Cl[C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:28][CH3:29])=[C:24]([Cl:27])[CH:25]=2)[N:20]=[C:19]([CH3:30])[C:18]=1[CH3:31]>>[Br:1][C:2]1[CH:7]=[C:6]2[N:8]([C:17]3[C:26]4[C:21](=[CH:22][C:23]([O:28][CH3:29])=[C:24]([Cl:27])[CH:25]=4)[N:20]=[C:19]([CH3:30])[C:18]=3[CH3:31])[CH2:9][C:10]3([CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1
Reactant: Brc1ccc2c(c1)NCC21CCOCC1
Reactant: COc1cc2nc(C)c(C)c(Cl)c2cc1Cl
Product: COc1cc2nc(C)c(C)c(N3CC4(CCOCC4)c4ccc(Br)cc43)c2cc1Cl

Procedure:
Prepared according to procedure M using 6-bromo-2′,3′,5′,6′-tetrahydrospiro-[indoline-3,4′-pyran] (0.3 g, 1.12 mmol) and 4,6-dichloro-7-methoxy-2,3-dimethylquinoline (0.3152 g, 1.23 mmol) to give 6-bromo-1-(6-chloro-7-methoxy-2,3-dimethyl-4-quinolinyl)-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-pyran] as a: 1H NMR (500 MHz, DMSO-d6) δ ppm 7.65 (1H, s), 7.58 (1H, s), 7.21 (1H, d, J=8.1 Hz), 6.82 (1H, dd, J=7.8, 1.7 Hz), 5.90 (1H, d, J=1.7 Hz), 3.96-4.05 (4H, m), 3.82-3.92 (3H, m), 3.41-3.53 (2H, m), 2.66 (3H, s), 2.17 (3H, s), 1.95-2.06 (2H, m), 1.85 (1H, dd, J=13.4, 1.7 Hz), 1.72 (1H, dd, J=13.3, 1.8 Hz); Mass Spectrum (ESI) m/e=487.0 [M+1 (79Br)] and 489.1 [M+1 (81Br)].