Ammonium Chloride → HCID 67398402, compound

HRID 70709Notes

Reaction equation

HRID 70709 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:15]1([S:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([C:27]3[NH:32][C:31](=[O:33])[C:30]([C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=3)=[O:26])=[CH:21][CH:20]=2)[CH2:17][CH2:16]1.[Cl-].[NH4+]>C(Cl)(Cl)Cl>[CH:15]1([S:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]([OH:26])[C:27]3[NH:32][C:31](=[O:33])[C:30]([C:34]([F:36])([F:35])[F:37])=[CH:29][CH:28]=3)=[CH:21][CH:20]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5049666Sodium triacetoxyborohydrideHCID 67399727HCID 67399727, compound

Product 1

HCID 67398402HCID 67398402, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Sodium triacetoxyborohydride (125 mg) was added to a solution of 6-{[4-(cyclopropylsulfanyl)phenyl]carbonyl}-3-(trifluoromethyl)pyridin-2(1H)-one (110 mg) in chloroform (3 mL), and the mixture was stirred at room temperature overnight. An ammonium chloride solution was added to the reaction solution, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate only) to give 6-{[4-(cyclopropylsulfanyl)phenyl](hydroxy)methyl}-3-(trifluoromethyl)pyridin-2(1H)-one (40 mg, 36%).

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate only)

Sources & evidence

ORD record
ord-b57227c17d40432ea13c02db8d4882f1
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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