Sodium borohydride → HCID 20786230, compound

HRID 2182679Notes

Reaction equation

HRID 2182679 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH3:34])=[C:6]([C:8]([CH3:32])([CH3:31])[CH2:9][C:10]([OH:30])([C:26]([F:29])([F:28])[F:27])[CH:11]=[N:12][C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:22]=2[N:21]=[C:20]([C:23]([NH2:25])=[O:24])[CH:19]=[CH:18]3)[CH:7]=1.[BH4-].[Na+]>CO.O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH3:34])=[C:6]([C:8]([CH3:31])([CH3:32])[CH2:9][C:10]([OH:30])([C:26]([F:28])([F:27])[F:29])[CH2:11][NH:12][C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:22]=2[N:21]=[C:20]([C:23]([NH2:25])=[O:24])[CH:19]=[CH:18]3)[CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 69203328HCID 69203328, compound

Product 1

HCID 20786230HCID 20786230, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

703 mg (1.47 mmol) of 8-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylidenamino]quinoline-2-carboxylic acid amide in 10 ml of methanol and 5.0 ml of tetrahydrofuran are mixed with 449 mg (11.8 mmol) of sodium borohydride. After 16 hours, the solvent is concentrated by evaporation, the residue is taken up in water and ethyl acetate, extracted with ethyl acetate, and the combined organic phases are dried on sodium sulfate. After removal of the solvent and purification on silica gel with hexane-ethyl acetate (0-50%) as well as dichloromethane-methanol (0-7%), 358 mg (51% of theory) of the product is obtained.

Workup

  1. concentrationthe solvent is concentrated by evaporation
  2. extractionethyl acetate, extracted with ethyl acetate
  3. customthe combined organic phases are dried on sodium sulfate
  4. customAfter removal of the solvent and purification on silica gel with hexane-ethyl acetate (0-50%) as well as dichloromethane-methanol (0-7%), 358 mg (51% of theory) of the product
  5. customis obtained

Sources & evidence

ORD record
ord-d85e1b2ff01f43f8a0b66b4499bc0459
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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