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

HRID 1258630Notes

Reaction equation

HRID 1258630 reaction equation
Cl.[Cl:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][NH:8]C(=O)OC(C)(C)C)=[CH:5][C:4]=1[NH:18][C:19]1[N:23]([CH3:24])[C:22]2[CH:25]=[C:26]([N:30]3[CH2:35][CH2:34][CH2:33][CH:32]([C:36]([F:39])([F:38])[F:37])[CH2:31]3)[C:27]([Cl:29])=[CH:28][C:21]=2[N:20]=1>O1CCOCC1.O.C([O-])([O-])=O.[K+].[K+]>[Cl:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][NH2:8])=[CH:5][C:4]=1[NH:18][C:19]1[N:23]([CH3:24])[C:22]2[CH:25]=[C:26]([N:30]3[CH2:35][CH2:34][CH2:33][CH:32]([C:36]([F:38])([F:37])[F:39])[CH2:31]3)[C:27]([Cl:29])=[CH:28][C:21]=2[N:20]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 67958331Tert-butyl N-{4-chloro-3-[5-chloro-1-methyl-6-(3-(trifluoromethyl)piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzyl}-carbamate

Product 1

HCID 679582014-Chloro-3-[5-chloro-1-methyl-6-(3-(trifluoromethyl)piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzylamine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 11430Potassium CarbonateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

4 M HCl in dioxane (20 mL) was added to tert-butyl N-{4-chloro-3-[5-chloro-1-methyl-6-(3-(trifluoromethyl)piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzyl}-carbamate (700 mg, 1.2 mmol) in dioxane (20 mL). The reaction mixture was stirred at rt for 2 h then diluted with water and aq. K2CO3-solution and stirred for 1 h at rt. The mixture was concentrated, filtered and the filtercake was washed with water and dried to give the sub-title compound.

Workup

  1. stirringstirred for 1 h at rt
  2. concentrationThe mixture was concentrated
  3. filtrationfiltered
  4. washthe filtercake was washed with water
  5. customdried

Sources & evidence

ORD record
ord-1cd21680026848aca74e2d57cd53e5a1
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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