Water → HCID 86672705, compound

HRID 2168523Notes

Reaction equation

HRID 2168523 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]1C(C)C.O.FC(F)(F)C(O)=O>C(Cl)Cl>[O:2]=[CH:3][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]=[CH:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 86672706HCID 86672706, compound

Product 1

HCID 86672705HCID 86672705, compoundYield 44%

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 D above in methylene chloride were added water and trifluoroacetic acid and the reaction was stirred at room temperature for 2 h and then heated at reflux for 3.5 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 1-(2-oxoethyl)-1H-benzo[d]imidazole-7-carboxylate (0.2 g, 44% over two steps): 1H NMR (500 MHz, DMSO-d6) δ 9.69 (s, 1H), 7.97 (dd, J=8.0, 1.0 Hz, 1H), 7.81 (dd, J=7.5, 1.0 Hz, 1H), 7.33 (t, J=8.0 Hz, 1H), 5.48 (s, 2H), 3.84 (s, 3H); MS (ESI+) m/z 218 (M+H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3.5 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-887c6ce45a2e45b7a7ae90b0ca64271f
Source dataset
uspto-grants-2015_06
Patent number
US09045501B2

Reaction notes

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