Diisopropylcarbodiimide → N-{4-Chloro-3-[5-chloro-6-(3-cyano-pyrrolidin-1-yl)-1H-benzimidazol-2-ylamino]-benzyl}2,2-dimethyl-propionamide

HRID 1258663Notes

Reaction equation

HRID 1258663 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])=[CH:4][C:3]=1[N:16]=[C:17]=S.[NH2:19][C:20]1[C:25]([NH2:26])=[CH:24][C:23]([N:27]2[CH2:31][CH2:30][CH:29]([C:32]#[N:33])[CH2:28]2)=[C:22]([Cl:34])[CH:21]=1.CC(C)N=C=NC(C)C>CN(C=O)C>[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])=[CH:4][C:3]=1[NH:16][C:17]1[NH:26][C:25]2[CH:24]=[C:23]([N:27]3[CH2:31][CH2:30][CH:29]([C:32]#[N:33])[CH2:28]3)[C:22]([Cl:34])=[CH:21][C:20]=2[N:19]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 679576781-(4,5-Diamino-2-chloro-phenyl)-pyrrolidine-3-carbonitrileHCID 86646343HCID 86646343, compound

Product 1

HCID 178447320N-{4-Chloro-3-[5-chloro-6-(3-cyano-pyrrolidin-1-yl)-1H-benzimidazol-2-ylamino]-benzyl}2,2-dimethyl-propionamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from N-(4-chloro-3-isothiocyanatobenzyl)-2,2-dimethyl-propionamide (66 mg, 0.2 mmol), 1-(4,5-diamino-2-chloro-phenyl)-pyrrolidine-3-carbonitrile (55 mg, 0.2 mmol) in DMF (2 mL) and DIC (39 μL, 0.2 mmol) in analogy to example 6 step (c).

Sources & evidence

ORD record
ord-81e4e20bb9eb471286222c250654bf03
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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