Hydrochloric Acid → HCID 178466828, compound

HRID 872735Notes

Reaction equation

HRID 872735 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:10]=[C:9]([C:11]([NH:13][C@@H:14]([CH3:31])[CH2:15][N:16]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([C:28]#[N:29])=[C:23]([Cl:30])[CH:22]=3)=[N:17]2)=[O:12])[NH:8][N:7]=1)(=[O:5])[CH3:4].Cl>C(O)C>[Cl:30][C:23]1[CH:22]=[C:21]([C:18]2[CH:19]=[CH:20][N:16]([CH2:15][C@@H:14]([NH:13][C:11]([C:9]3[NH:8][N:7]=[C:6]([CH:3]([OH:5])[CH3:4])[CH:10]=3)=[O:12])[CH3:31])[N:17]=2)[CH:26]=[C:25]([F:27])[C:24]=1[C:28]#[N:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 66576367(S)-3-acetyl-N-(1-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-pyrazole-5-carboxamide

Product 1

HCID 178466828HCID 178466828, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium borohydride (8.21 mg, 0.217 mmol) was added into a flask under nitrogen atmosphere. Dry ethanol was added and the mixture was stirred. (S)-3-acetyl-N-(1-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-pyrazole-5-carboxamide (45 mg, 0.108 mmol) in dry ethanol was added slowly and the mixture was stirred at RT for 2.5 h. pH of the reaction mixture was adjusted to ˜2 by addition of 1M HCl and the mixture was evaporated to dryness. The product was purified by Flash-chromatography. Yield 57.5%. 1H-NMR (400 MHz; DMSO): 1.13 (d, 3H), 1.37 (d, 3H), 4.22-4-51 (m, 3H), 4.73-4.85 (m, 1H), 5.38 (d, 1H), 6.39 (s, 1H), 6.99 (d, 1H), 7.82 (d, 1H), 7.86 (d, 1H), 7.97 (d, 1H), 8.09 (d, 1H), 13.00 (s, 1H)

Workup

  1. stirringthe mixture was stirred at RT for 2.5 h. pH of the reaction mixture
  2. customthe mixture was evaporated to dryness
  3. customThe product was purified by Flash-chromatography

Sources & evidence

ORD record
ord-861e9ae42b754e6ba843e15a24f5301e
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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