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

HRID 50274Notes

Reaction equation

HRID 50274 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:14])[CH2:10]C(O)=O)=[CH:5][CH:4]=1)#[N:2].[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]([CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:22](=[O:32])[C:23]1[CH:28]=[CH:27][C:26]([NH:29][CH3:30])=[C:25]([NH2:31])[CH:24]=1.Cl[CH2:41]Cl.CO>>[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]([CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:22]([C:23]1[CH:28]=[CH:27][C:26]2[N:29]([CH3:41])[C:30]([CH2:14][N:9]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[CH3:10])=[N:31][C:25]=2[CH:24]=1)=[O:32]

Participants

4

Reactant 3

HCID 11982993N-(3-Amino-4-(methylamino)benzoyl)-N-2-pyridinyl-beta-alanine ethyl esterHCID 18412499n-(4-Cyanophenyl)-n-methylglycineHCID 21226129Dichloromethane methanol

Product 1

HCID 184123561-Methyl-2-[N-(4-cyanophenyl)-N-methyl-aminomethyl]-benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)-amideYield 71%

Procedure

Prepared analogously to Example 25c from N-(4-cyanophenyl)-N-methylglycine and 3-amino-4-methylaminobenzoic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide. Yield: 71% of theory; Rf value: 0.66 (silica gel; dichloromethane/methanol=19:1).

Sources & evidence

ORD record
ord-080d1e32b7414be69126eae695f884b2
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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