Diisopropylcarbodiimide → N-{2-Fluoro-4-chloro-3-[5-chloro-1-methyl-6-(4-fluoro-piperidin-1-yl)-1H-benzimidazol-2-ylamino]-benzyl}-2,2-dimethyl-propionamide

HRID 1258689Notes

Reaction equation

HRID 1258689 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][NH:7][C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10])=[C:4]([F:16])[C:3]=1[N:17]=[C:18]=S.[Cl:20][C:21]1[C:22]([N:30]2[CH2:35][CH2:34][CH:33]([F:36])[CH2:32][CH2:31]2)=[CH:23][C:24]([NH:28][CH3:29])=[C:25]([CH:27]=1)[NH2:26].CC(C)N=C=NC(C)C>>[F:16][C:4]1[C:3]([NH:17][C:18]2[N:28]([CH3:29])[C:24]3[CH:23]=[C:22]([N:30]4[CH2:31][CH2:32][CH:33]([F:36])[CH2:34][CH2:35]4)[C:21]([Cl:20])=[CH:27][C:25]=3[N:26]=2)=[C:2]([Cl:1])[CH:15]=[CH:14][C:5]=1[CH2:6][NH:7][C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 56840194N-(2-fluoro-4-chloro-3-isothiocyanato-benzyl)-2,2-dimethyl-propionamideHCID 679579855-Chloro-2-methylamino-4-(4-fluoropiperidin-1-yl)-aniline

Product 1

HCID 67975177N-{2-Fluoro-4-chloro-3-[5-chloro-1-methyl-6-(4-fluoro-piperidin-1-yl)-1H-benzimidazol-2-ylamino]-benzyl}-2,2-dimethyl-propionamideYield 49%

Procedure

The title compound is prepared from N-(4-chloro-2-fluoro-3-isothiocyanato-benzyl)-2,2-dimethyl-propionamide and 5-chloro-2-methylamino-4-(4-fluoropiperidin-1-yl)-aniline and DIC in analogy to example 51.

Sources & evidence

ORD record
ord-9f6973969ba6445a8723045f3e0470db
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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