Ammonium Chloride → N-((S)-1-(3-(4-cyano-3,5-difluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(1-hydroxyethyl)-1H-pyrazole-3-carboxamide

HRID 872876Notes

Reaction equation

HRID 872876 reaction equation
[C:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([NH:11][C@@H:12]([CH3:29])[CH2:13][N:14]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[C:23]([F:25])[C:22]([C:26]#[N:27])=[C:21]([F:28])[CH:20]=3)=[N:15]2)=[O:10])[CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[C:26]([C:22]1[C:23]([F:25])=[CH:24][C:19]([C:16]2[CH:17]=[CH:18][N:14]([CH2:13][C@@H:12]([NH:11][C:9]([C:6]3[CH:5]=[C:4]([CH:1]([OH:3])[CH3:2])[NH:8][N:7]=3)=[O:10])[CH3:29])[N:15]=2)=[CH:20][C:21]=1[F:28])#[N:27]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 178466830HCID 178466830, compound

Product 1

HCID 70657301N-((S)-1-(3-(4-cyano-3,5-difluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(1-hydroxyethyl)-1H-pyrazole-3-carboxamideYield 3.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-5-acetyl-N-(1-(3-(4-cyano-3,5-difluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-pyrazole-3-carboxamide (200 mg, 0.50 mmol) was dissolved in ethanol (10 ml) and sodiumborohydride (95 mg, 2.51 mmol) was added. The reaction mixture was refluxed for 2 h, cooled and saturated ammonium chloride (20 ml) was added. The mixture was extracted three times with ethyl acetate and the combined organic fractions were washed with water, dried and evaporated. The residue was purified twice with reversed phase flash chromatography to afford (6.7 mg, 3%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 1.13 (d, 3H), 1.37 (d, 3H), 4.24-4.40 (m, 2H), 4.39-4.53 (m, 1H), 4.72-4.84 (m, 1H), 6.47 (s, 1H), 6.98 (m, 1H), 7.71-7.80 (m, 2H), 7.79-7.88 (d, 1H), 8.15 (d, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. temperaturecooled
  3. extractionThe mixture was extracted three times with ethyl acetate
  4. washthe combined organic fractions were washed with water
  5. customdried
  6. customevaporated
  7. customThe residue was purified twice with reversed phase flash chromatography

Sources & evidence

ORD record
ord-190bed323cb84b34a536632b376662ce
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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