Water → HCID 178428629, compound

HRID 1748648Notes

Reaction equation

HRID 1748648 reaction equation
[BH4-].[Na+].[F:3][C:4]1[C:5]([N:14]2[C:18]([CH3:19])=[C:17]([C:20]([NH:22][C:23]3[CH:24]=[N:25][C:26]([CH:30]4[CH2:35][CH2:34][C:33](=[O:36])[CH2:32][CH2:31]4)=[C:27]([CH3:29])[CH:28]=3)=[O:21])[CH:16]=[N:15]2)=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1.O>CO>[F:3][C:4]1[C:5]([N:14]2[C:18]([CH3:19])=[C:17]([C:20]([NH:22][C:23]3[CH:24]=[N:25][C:26]([C@H:30]4[CH2:31][CH2:32][C@H:33]([OH:36])[CH2:34][CH2:35]4)=[C:27]([CH3:29])[CH:28]=3)=[O:21])[CH:16]=[N:15]2)=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86692578HCID 86692578, compound

Product 1

HCID 178428629HCID 178428629, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (116.8 mg) was added under ice-cooling to a solution of 1-[3-fluoro-5-(trifluoromethyl)pyridin-2-yl]-5-methyl-N-[5-methyl-6-(4-oxocyclohexan-1-yl)pyridin-3-yl]-1H-pyrazole-4-carboxamide (211 mg) described in Example F34 in methanol (3 ml) and stirred at the same temperature for 30 minutes. After the reaction, water was added and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was fractionated with HPLC (water-acetonitrile:containing 0.05% trifluoroacetic acid). The obtained fraction was neutralized by the addition of 10% sodium carbonate, and the precipitates was filtered and dried at 60° C. under current of air to give the titled compound (92 mg) as a white solid.

Workup

  1. additionwas added
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. additionThe resulting residue was fractionated with HPLC (water-acetonitrile:containing 0.05% trifluoroacetic acid)
  6. additionThe obtained fraction was neutralized by the addition of 10% sodium carbonate
  7. filtrationthe precipitates was filtered
  8. customdried at 60° C. under current of air

Sources & evidence

ORD record
ord-303771e177004cd29bbc7419f7130ecc
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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