Trifluoroacetic acid → 4-Chloro-3-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzylamine

HRID 1258719Notes

Reaction equation

HRID 1258719 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7]C(=O)OC(C)(C)C)=[CH:4][C:3]=1[NH:17][C:18]1[N:22]([CH3:23])[C:21]2[CH:24]=[C:25]([N:29]3[CH2:34][CH2:33][CH:32]([C:35]([F:38])([F:37])[F:36])[CH2:31][CH2:30]3)[C:26]([Cl:28])=[CH:27][C:20]=2[N:19]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH2:7])=[CH:4][C:3]=1[NH:17][C:18]1[N:22]([CH3:23])[C:21]2[CH:24]=[C:25]([N:29]3[CH2:30][CH2:31][CH:32]([C:35]([F:37])([F:36])[F:38])[CH2:33][CH2:34]3)[C:26]([Cl:28])=[CH:27][C:20]=2[N:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67975169Tert-butyl N-{4-chloro-3-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzyl}-carbamate

Product 1

HCID 679580774-Chloro-3-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl N-{4-chloro-3-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzyl}-carbamate (790 mg, 1.38 mmol), TFA (1.54 mL, 20.7 mmol) and DCM (30 mL) was stirred at rt overnight. The mixture was cooled to 0° C., basicified to pH ˜10 and extracted with DCM. The organic layer was dried over Na2SO4, filtered and concentrated and the residue was washed with Et2O/PE.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washthe residue was washed with Et2O/PE

Sources & evidence

ORD record
ord-40cba123804144c1b6439f752fa1e518
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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