Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [C:1]([NH:4][C@H:5]([CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[C:6](OCC)=[O:7])(=[O:3])[CH3:2].[BH4-].[Na+].Cl>C(O)C.O>[OH:7][CH2:6][C@H:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1
Reactant: CCOC(=O)[C@@H](Cc1cccnc1)NC(C)=O
Agent: Cl
Agent: [BH4-]
Agent: [Na+]
Solvent: O
Solvent: CCO
Product: CC(=O)N[C@@H](CO)Cc1cccnc1
Temperature: 25 °C
Reaction time: 16 h
Yield: 65.3 %

Procedure:
A solution, under an inert atmosphere, of 20.77 g of ethyl (2R)-2-(acetylamino)-3-(3-pyridyl)propanoate in 208 cm3 of anhydrous ethanol is cooled to a temperature in the region of 10° C., followed by portionwise addition of 8.31 g of sodium borohydride. The reaction mixture is stirred for 16 hours at room temperature. The ethanol is evaporated off under reduced pressure (2 kPa) at a temperature in the region of 40° C., to give 43.56 g of a pale yellow paste which is taken up and stirred in 50 cm3 of water. The solution, which has a pH in the region of 12, is cooled to a temperature in the region of 0° C. and then neutralized by dropwise addition of concentrated hydrochloric acid. The resulting mixture is stirred for 1 hour at this temperature and the white precipitate formed is then filtered off on a sinter funnel, then dried in an oven under vacuum (0.1 kPa) at a temperature in the region of 55° C. 11.15 g of N-[(1R)-2-hydroxy-1-(3-pyridylmethyl)ethyl]acetamide are obtained in the form of a white solid melting at a temperature above 260° C. The filtrate is extracted with 3 times 100 cm3 of ethyl acetate and the organic phases are then combined, dried over magnesium sulfate, filtered and evaporated under reduced pressure (2 kPa) at a temperature in the region of 40° C. 2.4 g of N-[(1R)-2-hydroxyl-1-(3-pyridylmethyl)ethyl]acetamide partially complexed with boron are obtained in the form of a white paste. [1H NMR spectrum (300 MHz, (CD3)2SO-d6, δ in ppm): 1.75 (s: 3H); 2.61 (dd, J=14 and 9 Hz: 1H); 2.88 (dd, J=14 and 5.5 Hz: 1H); from 3.20 to 3.45 (mt: 2H); 3.91 (mt: 1H); 4.82 (broad t, J=5 Hz: 1H); 7.30 (dd, J=7.5 and 5 Hz: 1H); 7.62 (dt, J=7.5 and 2 Hz: 1H); 7.72 (d, J=9 Hz: 1H); from 8.35 to 8.45 (mt: 2H)].
Reaction SMILES: [NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([OH:10])[C:4]=2[CH:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:17][O:18][C:19](=[O:35])[CH:20]([N:27]1[C:32](=[O:33])[CH:31]=[C:30](I)[CH:29]=[N:28]1)[CH2:21][CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>CN(C)C=O>[CH3:17][O:18][C:19](=[O:35])[CH:20]([N:27]1[C:32](=[O:33])[CH:31]=[C:30]([O:10][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[CH:3]=[CH:2][NH:1]3)[CH:29]=[N:28]1)[CH2:21][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26]1
Reactant: Oc1cccc2[nH]ccc12
Reactant: COC(=O)C(CC1CCCC1)n1ncc(I)cc1=O
Agent: O=C([O-])[O-]
Agent: [K+]
Solvent: CN(C)C=O
Product: COC(=O)C(CC1CCCC1)n1ncc(Oc2cccc3[nH]ccc23)cc1=O
Temperature: 120 °C

Procedure:
A solution of 1H-indol-4-ol (3.5 g, 26.6 mmol) in N,N-dimethylformamide (40 mL) was treated with potassium carbonate (5.4 g, 39 mmol) and 3-cyclopentyl-2-(4-iodo-6-oxo-6H-pyridazin-1-yl)-propionic acid methyl ester (Intermediate 73 step 2.10 g, 26.6 mmol). The resulting reaction mixture was heated to 120° C. for 2 h. At this time, the reaction was cooled to 25° C. and then concentrated in vacuo. The residue was partitioned between water and methylene chloride. The aqueous phase was back extracted with methylene chloride. The combined organics was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Chromatography afforded 3-cyclopentyl-2-[4-(1H-indol-4-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl ester as a light oil (6.1 g, 60%).
Reaction SMILES: COC1C=C(OC)C=CC=1C[N:6]([C:31]1[CH:36]=[CH:35][N:34]=[CH:33][N:32]=1)[S:7]([C:10]1[CH:15]=[C:14]([F:16])[C:13]([O:17][C@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]2[C:24]2[CH:29]=[CH:28][N:27]=[N:26][CH:25]=2)=[CH:12][C:11]=1[F:30])(=[O:9])=[O:8].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[F:30][C:11]1[CH:12]=[C:13]([O:17][C@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]2[C:24]2[CH:29]=[CH:28][N:27]=[N:26][CH:25]=2)[C:14]([F:16])=[CH:15][C:10]=1[S:7]([NH:6][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][N:32]=1)(=[O:8])=[O:9]
Reactant: COc1ccc(CN(c2ccncn2)S(=O)(=O)c2cc(F)c(O[C@H]3CCCC[C@@H]3c3ccnnc3)cc2F)c(OC)c1
Agent: CC[SiH](CC)CC
Solvent: O=C(O)C(F)(F)F
Solvent: ClCCl
Product: O=S(=O)(Nc1ccncn1)c1cc(F)c(O[C@H]2CCCC[C@@H]2c2ccnnc2)cc1F
Yield: 95.8 %

Procedure:
The reaction and aftertreatment were conducted in the same manner as in Example 1b by using the N-(2,4-dimethoxybenzyl)-2,5-difluoro-4-{[(1S*,2R*)-2-(pyridazin-4-yl)cyclohexyl]oxy}-N-(pyrimidin-4-yl)benzenesulfonamide (0.04 g, 0.07 mmol) prepared in Example 53c, triethylsilane (0.06 mL), trifluoroacetic acid (0.07 mL) and dichloromethane (0.74 mL), to yield the title compound (30 mg, 94%) as a colorless solid.