Trifluoroacetic acid → HCID 70139538, compound

HRID 1533805Notes

Reaction equation

HRID 1533805 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([NH:17][C:18]([C:20]3[CH:42]=[CH:41][C:23]([C:24]([N:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]4[O:35][CH2:36][C:37]([CH3:40])([CH3:39])[N:38]=4)[CH3:27])=[O:25])=[CH:22][C:21]=3[O:43][CH3:44])=[O:19])[C:11]=2[N:10]=[CH:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([NH:17][C:18]([C:20]3[CH:42]=[CH:41][C:23]([C:24]([N:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]4[O:35][CH2:36][C:37]([CH3:40])([CH3:39])[N:38]=4)[CH3:27])=[O:25])=[CH:22][C:21]=3[O:43][CH3:44])=[O:19])[C:11]=2[N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70120934HCID 70120934, compound

Product 1

HCID 70139538HCID 70139538, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[N-[1-[(tert-butyl)oxycarbonyl]-benzimidazol-4-yl]carbamoyl]-N-[2-[4,4-dimethyl(2,5-oxazolinyl)]phenyl]-3-methoxy-N-methylbenzamide (400 mg) in dichloromethane (10 ml) was added trifluoroacetic acid (4 ml). The mixture was stirred at ambient temperature for 3 hours. The reaction mixture was concentrated in vacuo and the residue was diluted with a mixture of chloroform and saturated aqueous sodium bicarbonate solution. The organic layer was separated and washed with water and brine. The solution was dried over magnesium sulfate and the solvent was evaporated in vacuo. The residue was purified by column chromatography (chloroform:methanol=100:3) to give 4-[N-(1H-benzimidazol-4-yl)carbamoyl]-N-[2-[4,4-dimethyl(2,5-oxazolinyl)]phenyl]-3-methoxy-N-methylbenzamide (290 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted with a mixture of chloroform and saturated aqueous sodium bicarbonate solution
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialThe solution was dried over magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by column chromatography (chloroform:methanol=100:3)

Sources & evidence

ORD record
ord-f2249b2e13fe4f35bbd0095259be1fda
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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