Diisopropylcarbodiimide → 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

HRID 1258679Notes

Reaction equation

HRID 1258679 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([N:16]=[C:17]=S)[C:10]=1[Cl:19])([CH3:4])([CH3:3])[CH3:2].[Cl:21][C:22]1[C:23]([N:31]2[CH2:36][CH2:35][CH2:34][CH:33]([C:37]([F:40])([F:39])[F:38])[CH2:32]2)=[CH:24][C:25]([NH:29][CH3:30])=[C:26]([CH:28]=1)[NH2:27].CC(C)N=C=NC(C)C>CC#N>[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([NH:16][C:17]2[N:29]([CH3:30])[C:25]3[CH:24]=[C:23]([N:31]4[CH2:36][CH2:35][CH2:34][CH:33]([C:37]([F:39])([F:40])[F:38])[CH2:32]4)[C:22]([Cl:21])=[CH:28][C:26]=3[N:27]=2)[C:10]=1[Cl:19])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 56840196(2,4-Dichloro-3-isothiocyanato-benzyl)-carbamic acid tert-butyl esterHCID 679576925-Chloro-2-methylamino-4-(3-(trifluoromethyl)piperidin-1-yl)aniline

Product 1

HCID 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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared from (2,4-dichloro-3-isothiocyanato-benzyl)-carbamic acid tert-butyl ester (5.47 g, 16.4 mmol), 5-chloro-2-methylamino-4-(3-(trifluoromethyl)piperidin-1-yl)aniline (5.05 g, 16.4 mmol) and DIC 4.48 ml, 29 mmol) in MeCN in analogy to example 6 step (c).

Sources & evidence

ORD record
ord-eb1107fed98b49369f0e3321f82e1200
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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