Sodium borohydride → HCID 11657239, compound

HRID 1348560Notes

Reaction equation

HRID 1348560 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:44])([F:43])[C:5]1[CH:6]=[C:7]([C:15]([CH3:42])([CH3:41])[C:16]([N:18]([C:20]2[CH:21]=[N:22][C:23]([N:34]3[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]3)=[CH:24][C:25]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH:32]=[O:33])[CH3:19])=[O:17])[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1>CO.[Cl-].[Na+].O>[F:44][C:4]([F:3])([F:43])[C:5]1[CH:6]=[C:7]([C:15]([CH3:42])([CH3:41])[C:16]([N:18]([C:20]2[CH:21]=[N:22][C:23]([N:34]3[CH2:35][CH2:36][N:37]([CH3:40])[CH2:38][CH2:39]3)=[CH:24][C:25]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:32][OH:33])[CH3:19])=[O:17])[CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 21091639HCID 21091639, compound

Product 1

HCID 11657239HCID 11657239, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of 15 mg (0.41 mmol) sodium borohydride in 2 ml methanol were added at 0° C. 200 mg (0.338 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[4-(2-formyl-phenyl)-6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-N-methyl-isobutyramide. After stirring at 0° C. for 1 h 1 ml brine was added at 0° C. The mixture was stirred for 30 min. Methanol was distilled off and the residue was diluted with 20 ml ethyl acetate and washed with 20 ml brine. The organic layer was dried over sodium sulfate, concentrated and purified by flash chromatography to give 137 mg (68%) of the title compound as a light brown solid.

Workup

  1. additionwere added at 0° C
  2. additionwas added at 0° C
  3. distillationMethanol was distilled off
  4. additionthe residue was diluted with 20 ml ethyl acetate
  5. washwashed with 20 ml brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-3fa8f07b29844bf59d1eb19e2e2c9e6f
Source dataset
uspto-grants-2007_05
Patent number
US07211579B2

Reaction notes

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