Hydrochloric Acid → 2,4-Dichloro-3-[5-chloro-1-methyl-6-(3-(trifluoromethyl)piperidin-1-yl)-1H-benzimidazol-2-ylamino]benzylamine

HRID 1258680Notes

Reaction equation

HRID 1258680 reaction equation
Cl.C(OC(=O)[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([NH:17][C:18]2[N:22]([CH3:23])[C:21]3[CH:24]=[C:25]([N:29]4[CH2:34][CH2:33][CH2:32][CH:31]([C:35]([F:38])([F:37])[F:36])[CH2:30]4)[C:26]([Cl:28])=[CH:27][C:20]=3[N:19]=2)[C:11]=1[Cl:39])(C)(C)C>O1CCOCC1>[Cl:39][C:11]1[C:12]([NH:17][C:18]2[N:22]([CH3:23])[C:21]3[CH:24]=[C:25]([N:29]4[CH2:34][CH2:33][CH2:32][CH:31]([C:35]([F:38])([F:37])[F:36])[CH2:30]4)[C:26]([Cl:28])=[CH:27][C:20]=3[N:19]=2)=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=1[CH2:9][NH2:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86674334N-{2,4-Dichloro-3-[5-chloro-1-methyl-6-(3-(trifluoromethyl)piperidin-1-yl)-1H-benzimidazol-2-ylamino]benzyl}-carbamic acid tert-butyl ester

Product 1

HCID 866743352,4-Dichloro-3-[5-chloro-1-methyl-6-(3-(trifluoromethyl)piperidin-1-yl)-1H-benzimidazol-2-ylamino]benzylamine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4 M HCl in dioxane (38 mL) was added to N-{2,4-dichloro-3-[5-chloro-1-methyl-6-(3-(trifluoromethyl)piperidin-1-yl)-1H-benzimidazol-2-ylamino]benzyl}-carbamic acid tert-butyl ester (5.4 g, 8.9 mmol) in dioxane (300 mL) and stirred at rt overnight. The reaction mixture was concentrated and the resulting residue was diluted with aq. NaHCO3-solution. The aq. phase was extracted with EtOAc, the organic phase was dried with Na2SO4 and concentrated.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe resulting residue was diluted with aq. NaHCO3-solution
  3. extractionThe aq. phase was extracted with EtOAc
  4. dry with materialthe organic phase was dried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fd56f015cb654c11a4748a557d730aa6
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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