Sodium borohydride → HCID 178523499, compound

HRID 1093812Notes

Reaction equation

HRID 1093812 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[CH:34]=[CH:33][CH:32]=[CH:31][C:6]=1[O:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:30])[CH2:15][NH:16][C:17]([C:19]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[NH:21][N:20]=2)=[O:18])[CH2:10][CH2:9]1)=[O:4]>CO.O>[OH:4][CH2:3][C:5]1[CH:34]=[CH:33][CH:32]=[CH:31][C:6]=1[O:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:30])[CH2:15][NH:16][C:17]([C:19]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[NH:21][N:20]=2)=[O:18])[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 178519541HCID 178519541, compound

Product 1

HCID 178523499HCID 178523499, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

NaBH4 (5 mg, 0.12 mmol) was added to stirred a mixture of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-formyl-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide (50 mg, 0.1 mmol) in MeOH (2 mL) and stirring was continued for 1 hr. The reaction mixture was diluted with water, extracted with ethyl acetate and dried over sodium sulfate. The organic layer was concentrated under reduced pressure to afford the residue. The residue was purified by recrystallisation from CHCl3 in hexane mixture to afford 25 mg (58% yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-hydroxymethyl-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 435.2, 93.8%, 1H NMR (300 MHz, DMSO-d6): δ13.8 (m, 1H), 8.0 (m, 1H), 7.8 (m, 2H), 7.5 (m, 2H), 7.4 (m, 2H), 7.2 (m, 1H), 7.1 (m, 1H), 7.0 (m, 1H), 6.9 (m, 1H), 5.0 (m, 1H), 4.7 (m, 1H), 4.5 (m, 2H), 3.7 (m, 3H), 3.5 (m, 2H), 2.0 (m, 2H), 1.7 (m, 2H).

Workup

  1. stirringstirring
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customto afford the residue
  6. customThe residue was purified by recrystallisation from CHCl3 in hexane mixture

Sources & evidence

ORD record
ord-bd5c2956a50b4961a397d3deea8012d3
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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