Sodium borohydride → N-((S)-2-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propyl)-5-(1-hydroxyethyl)isoxazole-3-carboxamide

HRID 872699Notes

Reaction equation

HRID 872699 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[O:10][N:9]=[C:8]([C:11]([NH:13][CH2:14][C@@H:15]([N:17]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([Cl:30])[CH:23]=3)=[N:18]2)[CH3:16])=[O:12])[CH:7]=1)(=[O:5])[CH3:4]>C(O)C>[Cl:30][C:24]1[CH:23]=[C:22]([C:19]2[CH:20]=[CH:21][N:17]([C@@H:15]([CH3:16])[CH2:14][NH:13][C:11]([C:8]3[CH:7]=[C:6]([CH:3]([OH:5])[CH3:4])[O:10][N:9]=3)=[O:12])[N:18]=2)[CH:27]=[CH:26][C:25]=1[C:28]#[N:29]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67172077HCID 67172077, compound

Product 1

HCID 52919948N-((S)-2-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propyl)-5-(1-hydroxyethyl)isoxazole-3-carboxamideYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (6.41 mg, 0.169 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)-5-acetyl-N-(2-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propyl)isoxazole-3-carboxamide (33.7 mg, 0.085 mmol) was added and the reaction mixture was warmed slowly to RT while stirring overnight. The crude product was cooled to 0° C., the pH was adjusted to about 3 and the mixture was evaporated. 5% of DCM/MeOH was added and the crude product was washed with 1M NaHCO3, water and dried. Yield 96%. 1H-NMR (400 MHz; CDCl3): δ 1.57-1.65 (m, 3H) 3.75-3.84 (m, 1H), 3.87-3.95 (m, 1H), 4.57-4.67 (m, 1H), 5.03 (q, 1H), 6.61 (d, 1H), 6.62 (s, 1H), 7.50 (d, 1H), 7.56-7.63 (m, 1H), 7.65-7.69 (2× s, 1H), 7.81 (dd, 1H), 8.01 (d, 1H).

Workup

  1. additionwas added
  2. customthe mixture was evaporated
  3. addition5% of DCM/MeOH was added
  4. washthe crude product was washed with 1M NaHCO3, water
  5. customdried

Sources & evidence

ORD record
ord-16754fd3b3944d5aac9db3cbb1932026
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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