Sodium borohydride → HCID 68672945, compound

HRID 1927686Notes

Reaction equation

HRID 1927686 reaction equation
[BH4-].[Na+].[CH3:3][N:4]([CH3:37])[S:5]([N:8]1[CH:12]=[C:11]([C:13]([C:15]2([C:19]([F:22])([F:21])[F:20])[CH2:18][CH2:17][CH2:16]2)=[O:14])[N:10]=[C:9]1[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)=[CH:27][CH:26]=1)(=[O:7])=[O:6].C(OCC)(=O)C.CCCCCC>CO.O>[OH:14][CH:13]([C:15]1([C:19]([F:22])([F:21])[F:20])[CH2:16][CH2:17][CH2:18]1)[C:11]1[N:10]=[C:9]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)=[CH:27][CH:26]=2)[N:8]([S:5]([N:4]([CH3:3])[CH3:37])(=[O:7])=[O:6])[CH:12]=1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 21226206Ethyl acetate hexaneHCID 68673050HCID 68673050, compound

Product 1

HCID 68672945HCID 68672945, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

Sodium borohydride (8 mg, 0.21 mmol) was added to a solution of N,N-dimethyl-2-[2-(4-pyridin-2-ylphenyl)ethyl]-4-{[1-(trifluoromethyl)cyclobutyl]carbonyl}-1H-imidazole-1-sulfonamide (106 mg, 0.21 mmol) in methanol (3 mL) at 0° C. followed by 1 drop of water. The resulting solution was stirred at rt for 1 hr. The reaction mixture was partially concentrated and partitioned between 1N aqueous sodium hydroxide and ethyl acetate. The organic phase was washed with brine, dried (sodium sulfate) and concentrated to give a residue. Chromatography of the residue over silica gel eluting with 40-100% ethyl acetate/hexane afforded 4-{hydroxy[1-(trifluoromethyl)cyclobutyl]methyl)-N,N-dimethyl-2-[2-(4-pyridin-2-ylphenyl)ethyl]-1H-imidazole-1-sulfonamide.

Workup

  1. concentrationThe reaction mixture was partially concentrated
  2. custompartitioned between 1N aqueous sodium hydroxide and ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated
  6. customto give a residue

Sources & evidence

ORD record
ord-3843a28f938541adb2b6e108168b7e67
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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