Ethanol → HCID 67172696, compound

HRID 872662Notes

Reaction equation

HRID 872662 reaction equation
[BH4-].[Na+].C(O)C.[Cl:6][C:7]1[CH:8]=[C:9]([C:15]2[CH:19]=[CH:18][N:17]([CH2:20][C@@H:21]([NH:23][C:24]([C:26]3[N:27]=[C:28]([C:31](OCC)=[O:32])[S:29][CH:30]=3)=[O:25])[CH3:22])[N:16]=2)[CH:10]=[CH:11][C:12]=1[C:13]#[N:14]>O>[Cl:6][C:7]1[CH:8]=[C:9]([C:15]2[CH:19]=[CH:18][N:17]([CH2:20][C@@H:21]([NH:23][C:24]([C:26]3[N:27]=[C:28]([CH2:31][OH:32])[S:29][CH:30]=3)=[O:25])[CH3:22])[N:16]=2)[CH:10]=[CH:11][C:12]=1[C:13]#[N:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 86670248HCID 86670248, compound

Product 1

HCID 67172696HCID 67172696, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium borohydride (86 mg, 2.262 mmol) was added into a flask and the atmosphere was replaced with nitrogen. Dry ethanol was added and the reaction mixture was cooled to 0° C. (S)-ethyl 4-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-ylcarbamoyl)thiazole-2-carboxylate (502 mg, 1.131 mmol) was added and the reaction mixture was warmed slowly to RT while stirring overnight. The crude product was cooled to 0° C., water was added dropwise, the pH was adjusted to 7 and the mixture was evaporated. DCM and a few drops of methanol were added and the crude product was washed with 1M Na2CO3 and with water. Yield 58.6%. 1H-NMR (400 MHz; DMSO-d6): δ 1.12 (d, 3H), 4.31 (dd, 1H), 4.40 (dd, 1H), 4.43-4.51 (m, 1H), 4.79 (d, 2H), 6.20 (t, 1H), 6.95 (d, 1H), 7.84 (d, 1H), 7.96 (dd, 1H), 7.98 (dd, 1H), 8.08 (dd, 1H), 8.13 (s, 1H), 8.50 (d, 1H).

Workup

  1. additionwas added
  2. customthe mixture was evaporated
  3. additionDCM and a few drops of methanol were added
  4. washthe crude product was washed with 1M Na2CO3 and with water

Sources & evidence

ORD record
ord-8c3be261fe0f48b69364778935316d9b
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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