1,2-Dichloroethane → Tert-butyl N-{4-chloro-3-[5-chloro-1-methyl-6-(3-(trifluoromethyl)piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzyl}-carbamate

HRID 1258629Notes

Reaction equation

HRID 1258629 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:17]=[C:18]=S.[Cl:20][C:21]1[C:22]([N:30]2[CH2:35][CH2:34][CH2:33][CH:32]([C:36]([F:39])([F:38])[F:37])[CH2:31]2)=[CH:23][C:24]([NH:28][CH3:29])=[C:25]([CH:27]=1)[NH2:26].C(Cl)CCl>CC#N>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][C:3]=1[NH:17][C:18]1[N:28]([CH3:29])[C:24]2[CH:23]=[C:22]([N:30]3[CH2:35][CH2:34][CH2:33][CH:32]([C:36]([F:38])([F:39])[F:37])[CH2:31]3)[C:21]([Cl:20])=[CH:27][C:25]=2[N:26]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 679576925-Chloro-2-methylamino-4-(3-(trifluoromethyl)piperidin-1-yl)anilineHCID 86646335tert-Butyl 4-chloro-3-isothiocyanatobenzylcarbamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Tert-butyl 4-chloro-3-isothiocyanatobenzylcarbamate (938 mg, 3.1 mmol) was added to 5-chloro-2-methylamino-4-(3-(trifluoromethyl)piperidin-1-yl)aniline (920 mg, 3.0 mmol) in MeCN (20 mL). The mixture was stirred for 4 h at rt, then EDC (582 μL, 3.3 mmol) was added and it was stirred overnight. The reaction mixture was purified by chromatography to give the sub-title compound.

Workup

  1. stirringit was stirred overnight
  2. customThe reaction mixture was purified by chromatography

Sources & evidence

ORD record
ord-656261bf5aa9440e897464e14b02befb
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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