Sodium borohydride → N-((S)-2-(3-(3-chloro-4-cyano-2-methylphenyl)-1H-pyrazol-1-yl)propyl)-2-(1-hydroxyethyl)oxazole-4-carboxamide

HRID 872717Notes

Reaction equation

HRID 872717 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[O:7][CH:8]=[C:9]([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])[C:23]=3[CH3:31])=[N:18]2)[CH3:16])=[O:12])[N:10]=1)(=[O:5])[CH3:4]>C(O)C>[Cl:30][C:24]1[C:23]([CH3:31])=[C:22]([C:19]2[CH:20]=[CH:21][N:17]([C@@H:15]([CH3:16])[CH2:14][NH:13][C:11]([C:9]3[N:10]=[C:6]([CH:3]([OH:5])[CH3:4])[O:7][CH:8]=3)=[O:12])[N:18]=2)[CH:27]=[CH:26][C:25]=1[C:28]#[N:29]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67171858(S)-2-acetyl-N-(2-(3-(3-chloro-4-cyano-2-methylphenyl)-1H-pyrazol-1-yl)propyl)oxazole-4-carboxamide

Product 1

HCID 67172839N-((S)-2-(3-(3-chloro-4-cyano-2-methylphenyl)-1H-pyrazol-1-yl)propyl)-2-(1-hydroxyethyl)oxazole-4-carboxamideYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.055 g, 1.462 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)-2-acetyl-N-(2-(3-(3-chloro-4-cyano-2-methylphenyl)-1H-pyrazol-1-yl)propyl)oxazole-4-carboxamide (0.301 g, 0.731 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 6 and the mixture was evaporated. 5% of methanol/DCM was added and the crude product was washed with 1M NaHCO3 and with water. The mixture was dried and evaporated. Yield 94%. 1H-NMR (400 MHz; CDCl3): δ 1.57 (d, 3H), 1.61 (d, 3H), 3.78-3.83 (m, 1H), 3.87-3.94 (m, 1H), 4.59-4.68 (m, 1H), 4.87-4.96 (m, 1H), 6.43 (d, 1H), 7.34-7.42 (m, 1H), 7.51 (d, 1H), 7.54-7.61 (m, 2H), 8.14 (s, 1H).

Workup

  1. additionwas added
  2. customthe mixture was evaporated
  3. addition5% of methanol/DCM was added
  4. washthe crude product was washed with 1M NaHCO3 and with water
  5. customThe mixture was dried
  6. customevaporated

Sources & evidence

ORD record
ord-f392d177252041a399e78b55b57c7bc6
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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