Acetone → HCID 22992335, compound

HRID 1168332Notes

Reaction equation

HRID 1168332 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([C:13]([CH3:39])([CH3:38])[C:14]([N:16]([CH3:37])[C:17]2[CH:18]=[N:19][C:20]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][C:31]3=[O:36])=[CH:21][C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+].CC(C)=O>CO.O1CCCC1>[F:41][C:2]([F:1])([F:40])[C:3]1[CH:4]=[C:5]([C:13]([CH3:39])([CH3:38])[C:14]([N:16]([C:17]2[CH:18]=[N:19][C:20]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH:31]3[OH:36])=[CH:21][C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[CH3:37])=[O:15])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 10144852HCID 10144852, compoundHCID 21585214Cerium trichloride heptahydrate

Product 1

HCID 22992335HCID 22992335, compoundYield 17.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of 494 mg (0.852 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-[6-(3-oxo-morpholin-4-yl)-4-o-tolyl-pyridin-3-yl]-isobutyramide in 5 ml methanol and 5 ml tetrahydrofuran were added 635 mg (1.70 mmol) cerium(III)chloride heptahydrate. After stirring for 5 min, 64 mg (1.70 mmol) sodium borohydride were added in two portions within 2 min. After stirring for 3 h at 0° C., 1 ml acetone was added and stirring was continued for 10 min. The solvent was removed, the residue was re-dissolved in ethyl acetate and the organic phase was washed with saturated sodium carbonate solution, dried (magnesium sulfate) and evaporated. The crude material was purified by flash-chromatography to give 87 mg (16%) ofthe title compound as white crystals. MS m/e (%): 582 (M+H+, 100).

Workup

  1. stirringAfter stirring for 3 h at 0° C.
  2. stirringstirring
  3. waitwas continued for 10 min
  4. customThe solvent was removed
  5. dissolutionthe residue was re-dissolved in ethyl acetate
  6. washthe organic phase was washed with saturated sodium carbonate solution
  7. dry with materialdried (magnesium sulfate)
  8. customevaporated
  9. customThe crude material was purified by flash-chromatography

Sources & evidence

ORD record
ord-a7021cd15fe041d2bdc01f448bcd4b27
Source dataset
uspto-grants-2003_09
Patent number
US06624176B2

Reaction notes

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