Methanol → HCID 18470029, compound

HRID 2228450Notes

Reaction equation

HRID 2228450 reaction equation
FC(F)(F)C([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)=[O:15])=[CH:8][CH:7]=1)=O.C(=O)([O-])[O-].[K+].[K+].CO>O>[NH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][C:14]([C:16]2[CH:17]=[CH:18][C:19]([N:22]3[CH2:27][CH2:26][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][CH2:23]3)=[CH:20][CH:21]=2)=[O:15])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 18470012HCID 18470012, compound

Product 1

HCID 18470029HCID 18470029, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,2,2-trifluoro-N-(4-{3-[4-(4-methanesulfonylpiperazin-1-yl)-phenyl]-3-oxopropyl}phenyl)acetamide (0.43 g, 0.88 mmol), and a solution of potassium carbonate (0.61 g, 4.39 mmol) in water (10 mL), and methanol (20 mL) was warmed on a steam bath, then stirred at room temperature for about 12 hours. The reaction mixture was concentrated to one-third volume, diluted with cold water, and extracted with dichloromethane. The organic extract was washed with water, brine, dried, and concentrated in vacuo. Purification by silica gel chromatography, eluting with 2% methanol in dichloromethane gave the title compound as a white solid (0.28 g, 82%), m. p.166.5-170.0° C.

Workup

  1. concentrationThe reaction mixture was concentrated to one-third volume
  2. additiondiluted with cold water
  3. extractionextracted with dichloromethane
  4. extractionThe organic extract
  5. washwas washed with water, brine
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customPurification by silica gel chromatography
  9. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-eddee7a4b79a417cbf4186ea76ee1e81
Source dataset
uspto-grants-2002_07
Patent number
US06417186B1

Reaction notes

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