N-(4-Cyanophenyl)glycine → Ethyl 3-(((2-(((4-cyanophenyl)amino)methyl)-1-methyl-1H-benzimidazol-5-yl)carbonyl)pyridin-2-ylamino)propionate

HRID 50260Notes

Reaction equation

HRID 50260 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11](O)=O)=[CH:5][CH:4]=1)#[N:2].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:21](=[O:31])[C:22]1[CH:27]=[CH:26][C:25]([NH:28][CH3:29])=[C:24]([NH2:30])[CH:23]=1>ClCCl.CO>[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:21]([C:22]1[CH:27]=[CH:26][C:25]2[N:28]([CH3:29])[C:11]([CH2:10][NH:9][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)=[N:30][C:24]=2[CH:23]=1)=[O:31]

Participants

4

Reactant 2

HCID 817965N-(4-Cyanophenyl)glycineHCID 11982993N-(3-Amino-4-(methylamino)benzoyl)-N-2-pyridinyl-beta-alanine ethyl ester

Product 1

HCID 11627749Ethyl 3-(((2-(((4-cyanophenyl)amino)methyl)-1-methyl-1H-benzimidazol-5-yl)carbonyl)pyridin-2-ylamino)propionateYield 61%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 25c from N-(4-cyanophenyl)glycine and 3-amino-4-methylaminobenzoic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide. Yield: 61% of theory; Rf value: 0.62 (silica gel; dichloromethane/methanol=19:1).

Sources & evidence

ORD record
ord-48eed80ffa4b4fb899e778a34e676b41
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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