Water → HCID 86672709, compound

HRID 2369909Notes

Reaction equation

HRID 2369909 reaction equation
C[O:2][CH:3](OC)[CH2:4][N:5]1[C:9]2[C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH:18]([CH3:20])[CH3:19].O.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:18]([C:6]1[N:5]([CH2:4][CH:3]=[O:2])[C:9]2[C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=1)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 86672706HCID 86672706, compound

Product 1

HCID 86672709HCID 86672709, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 1-(2,2-dimethoxyethyl)-2-isopropyl-1H-benzo[d]imidazole-7-carboxylate from Step A above in methylene chloride and water was added trifluoroacetic acid and the reaction was stirred at room temperature for 1.5 h and then heated at reflux for 2 h. The reaction mixture was concentrated under reduced pressure to remove the excess trifluoroacetic acid, diluted with methylene chloride, washed with saturated aqueous sodium bicarbonate, re-extracted with methylene chloride, dried (Na2SO4), filtered, and concentrated under reduced pressure to give methyl 2-isopropyl-1-(2-oxoethyl)-1H-benzo[d]imidazole-7-carboxylate: 1H NMR (300 MHz, DMSO-d6) δ 9.69 (s, 1H), 7.87 (dd, J=8.1, 0.9 Hz, 7.68 (dd, J=7.5, 0.9 Hz, 1H), 7.26 (t, J=7.8 Hz, 1H), 5.44 (s, 2H), 3.84 (s, 3H), 3.22-3.17 (m, 1H), 1.34-1.27 (m, 6H); MS (ESI+) m/z 261 (M+H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customto remove the excess trifluoroacetic acid
  5. additiondiluted with methylene chloride
  6. washwashed with saturated aqueous sodium bicarbonate
  7. extractionre-extracted with methylene chloride
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f9c465b902a848248ce74908a62589c7
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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