Trifluoroacetic acid → 7-[(4-Chlorophenyl)(isopropyl)amino]-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 2235555Notes

Reaction equation

HRID 2235555 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:29]([CH3:31])[CH3:30])[C:9]2[C:14]3[N:15]([CH3:28])[C:16](=[O:27])[N:17](CC4C=CC(OC)=CC=4)[C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:29]([CH3:31])[CH3:30])[C:9]2[C:14]3[N:15]([CH3:28])[C:16](=[O:27])[NH:17][C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 685813547-[(4-chlorophenyl)(isopropyl)amino]-3-(4-methoxybenzyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 685810587-[(4-Chlorophenyl)(isopropyl)amino]-1-methyl-1,3-dihydro-2H-benzimidazol-2-oneYield 47.1%

Conditions

Temperature
65 °C

Procedure

To a mixture of 7-[(4-chlorophenyl)(isopropyl)amino]-3-(4-methoxybenzyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (80 mg, 0.18 mmol) and trifluoroacetic acid (3 ml) was stirred at 65° C. for 19 h. The mixture was concentrated in vacuo, diluted with saturated aqueous sodium bicarbonate (20 ml) and extracted with ethyl acetate (30 ml). The extract was washed with water, dried over magnesium sulfate and evaporated. The residue was flash chromatographed eluting with a 33% ethyl acetate/hexanes to give 26.8 mg (34%) of the title compound as an oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with saturated aqueous sodium bicarbonate (20 ml)
  3. extractionextracted with ethyl acetate (30 ml)
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customchromatographed
  8. washeluting with a 33% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-f6afa4d958764ce98360028c10b3d184
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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