N-(3-Amino-4-(methylamino)benzoyl)-N-2-pyridinyl-beta-alanine ethyl ester → 1-Methyl-2-[2-(2-cyanothiophen-5-yl)ethyl]benzimidazol-5-yl-carboxylic acid-n-(2-pyridyl)-n-(2-ethoxycarbonylethyl)amide

HRID 2288395Notes

Reaction equation

HRID 2288395 reaction equation
[C:1]([C:3]1[S:4][C:5]([CH2:8][CH2:9][C:10](O)=O)=[CH:6][CH:7]=1)#[N:2].[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:20](=[O:30])[C:21]1[CH:26]=[CH:25][C:24]([NH:27][CH3:28])=[C:23]([NH2:29])[CH:22]=1>ClCCl.CO>[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:20]([C:21]1[CH:26]=[CH:25][C:24]2[N:27]([CH3:28])[C:10]([CH2:9][CH2:8][C:5]3[S:4][C:3]([C:1]#[N:2])=[CH:7][CH:6]=3)=[N:29][C:23]=2[CH:22]=1)=[O:30]

Participants

4

Reactant 2

HCID 11982993N-(3-Amino-4-(methylamino)benzoyl)-N-2-pyridinyl-beta-alanine ethyl esterHCID 184125013-(5-Cyanothiophen-2-yl)propanoic acid

Product 1

HCID 184124051-Methyl-2-[2-(2-cyanothiophen-5-yl)ethyl]benzimidazol-5-yl-carboxylic acid-n-(2-pyridyl)-n-(2-ethoxycarbonylethyl)amideYield 18%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 25c from 3-(2-cyanothiophen-5-yl)-propionic acid and 3-amino-4-methylamino-benzoic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide. Yield: 18% of theory, Rf value: 0.66 (silica gel; dichloromethane/methanol=9:1)

Sources & evidence

ORD record
ord-535579c3a9f345cbaafbd5223ae32252
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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