Trifluoroacetic acid → N-(4-bromo-phenyl)-2-(2-chloro-5-{[amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid amide

HRID 1410246Notes

Reaction equation

HRID 1410246 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:37]([O:38][CH2:39][CH:40]([F:42])[F:41])=[CH:36][C:14]3[N:15]([CH3:35])[C:16]([NH:18][C:19]4[CH:24]=[C:23]([CH2:25][NH:26]C(OC(C)(C)C)=O)[CH:22]=[CH:21][C:20]=4[Cl:34])=[N:17][C:13]=3[CH:12]=2)=[O:10])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:37]([O:38][CH2:39][CH:40]([F:42])[F:41])=[CH:36][C:14]3[N:15]([CH3:35])[C:16]([NH:18][C:19]4[CH:24]=[C:23]([CH2:25][NH2:26])[CH:22]=[CH:21][C:20]=4[Cl:34])=[N:17][C:13]=3[CH:12]=2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86646339N-(4-Bromo-phenyl)-2-(2-chloro-5-{[(tert-butoxycarbonyl)-amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid amide

Product 1

HCID 59529876N-(4-bromo-phenyl)-2-(2-chloro-5-{[amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(4-bromo-phenyl)-2-(2-chloro-5-{[(tert-butoxycarbonyl)-amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid amide (1.35 g; 2.03 mmol) and TFA (3.47 g; 30.5 mmol) in DCM (75 mL) was stirred over night at rt. The mixture was cooled to 0° C. and basicified to pH ˜10 and extracted with DCM. The organic extracts were dried over Na2SO4, filtered and concentrated. The residue was washed with a mixture of Et2O and petroleum ether to give the sub-title compound.

Workup

  1. temperatureThe mixture was cooled to 0° C. and basicified to pH ˜10
  2. extractionextracted with DCM
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe residue was washed with a mixture of Et2O and petroleum ether

Sources & evidence

ORD record
ord-6384e2fdd33a48c0aea157071707954f
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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