Water → HCID 178429260, compound

HRID 1748644Notes

Reaction equation

HRID 1748644 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([CH3:16])=[C:14]([C:17]([NH:19][C:20]3[CH:21]=[N:22][C:23]([CH:26]4[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]4)=[CH:24][CH:25]=3)=[O:18])[CH:13]=[N:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>C(O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([CH3:16])=[C:14]([C:17]([NH:19][C:20]3[CH:21]=[N:22][C:23]([C@H:26]4[CH2:27][CH2:28][C@H:29]([OH:32])[CH2:30][CH2:31]4)=[CH:24][CH:25]=3)=[O:18])[CH:13]=[N:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86692584HCID 86692584, compound

Product 1

HCID 178429260HCID 178429260, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(4-tert-butylphenyl)-5-methyl-N-[6-(4-oxocyclohexyl)pyridin-3-yl]-1H-pyrazole-4-carboxamide (136 mg) in ethanol (5 ml) was cooled in ice water, sodium borohydride (48 mg) was added and stirred at the same temperature for an hour. 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 purified with a silica gel column chromatography (n-hexane/ethyl acetate), washed with ethanol, the resulting solid was filtered and dried at 60° C. in vacuo to give the titled compound (29 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. customThe resulting residue was purified with a silica gel column chromatography (n-hexane/ethyl acetate)
  6. washwashed with ethanol
  7. filtrationthe resulting solid was filtered
  8. customdried at 60° C. in vacuo

Sources & evidence

ORD record
ord-47c5df75e55948b586033175b7d8849e
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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