N-(4-Cyanophenyl)glycine → 1-Methyl-2-[n-(4-cyanophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-n-(2-pyridyl)-n-ethoxycarbonylmethylamide

HRID 50253Notes

Reaction equation

HRID 50253 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][C:33]([O:35][CH2:36][CH3:37])=[O:34])[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][C:33]([O:35][CH2:36][CH3:37])=[O:34])[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 184125383-Amino-4-methylaminobenzoic acid-n-(2-pyridyl)-n-ethoxycarbonylmethylamide

Product 1

HCID 184125571-Methyl-2-[n-(4-cyanophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-n-(2-pyridyl)-n-ethoxycarbonylmethylamideYield 24%

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-ethoxycarbonylmethylamide. Yield: 24% of theory; Rf value: 0.56 (silica gel; dichloromethane/methanol=4:1).

Sources & evidence

ORD record
ord-56cf75a9d0f340dda7254bf393c2a5f5
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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