Methanol → HCID 22063977, compound

HRID 1828179Notes

Reaction equation

HRID 1828179 reaction equation
[CH:1]1([N:6]2[C:10]3[CH:11]=[CH:12][C:13]([C:15](=O)[CH:16]([NH:24][C:25](=O)[CH2:26][CH2:27][O:28][CH3:29])[C:17]4[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=4)=[CH:14][C:9]=3[N:8]([CH3:32])[C:7]2=[O:33])[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C([O-])=O.[NH4+:41].CO>C(OCC)(=O)C>[CH:1]1([N:6]2[C:10]3[CH:11]=[CH:12][C:13]([C:15]4[NH:41][C:25]([CH2:26][CH2:27][O:28][CH3:29])=[N:24][C:16]=4[C:17]4[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=4)=[CH:14][C:9]=3[N:8]([CH3:32])[C:7]2=[O:33])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 887MethanolHCID 2724268Ammonium trifluoroacetateHCID 22063832HCID 22063832, compound

Product 1

HCID 22063977HCID 22063977, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-[2-(1-Cyclopentyl-3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-2-oxo-1-m-toly-ethyl]-3-methoxy-propionamide (294 mg, 0.65 mmol) was stirred with ammonium trifluoroacetate (857 mg, 6.5 mmol) and the mixture was heated to 150 deg C. in an oil bath. Occasionally, the sides of the flask were rinced down with methanol to insure all reactants were heated uniformly. A TLC (ethyl acetate) of the reaction mixture after 1 hour of heating showed complete reaction. The oil bath was removed, and hot water was added to the reaction mixture as it cooled. When the mixture reached room temperature, no precipitate formed, so the aqueous mixture was extracted with ethyl acetate (2×20 mL). The combined organic phase was washed with water and dried over anhydrous sodium sulfate to afford 240 mg of a tan solid. MS (M+1)=431.3.

Workup

  1. temperaturethe mixture was heated to 150 deg C
  2. temperaturewere heated uniformly
  3. customreaction
  4. customThe oil bath was removed
  5. additionhot water was added to the reaction mixture as it
  6. temperaturecooled
  7. customreached room temperature
  8. customno precipitate formed, so the aqueous mixture
  9. extractionwas extracted with ethyl acetate (2×20 mL)
  10. washThe combined organic phase was washed with water
  11. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-02565e4d1965413290b0ca62dc1291c3
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

Loading…