Benzoyl chloride → methyl 3-(N-[2-[[4-(N-benzoylcarbamimidoyl)anilino]methyl]-1-methylbenzimidazole-5-carbonyl]anilino)propanoate

HRID 50303Notes

Reaction equation

HRID 50303 reaction equation
Cl.[C:2]1([N:8]([CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])[C:9]([C:11]2[CH:31]=[CH:30][C:14]3[N:15]([CH3:29])[C:16]([CH2:18][NH:19][C:20]4[CH:25]=[CH:24][C:23]([C:26](=[NH:28])[NH2:27])=[CH:22][CH:21]=4)=[N:17][C:13]=3[CH:12]=2)=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:38](Cl)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>ClCCl.C(O)C>[C:2]1([N:8]([CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])[C:9]([C:11]2[CH:31]=[CH:30][C:14]3[N:15]([CH3:29])[C:16]([CH2:18][NH:19][C:20]4[CH:25]=[CH:24][C:23]([C:26](=[NH:27])[NH:28][C:38](=[O:45])[C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)=[CH:22][CH:21]=4)=[N:17][C:13]=3[CH:12]=2)=[O:10])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 184127011-Methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-methoxycarbonylethyl)amide Hydrochloride

Product 1

HCID 140435591methyl 3-(N-[2-[[4-(N-benzoylcarbamimidoyl)anilino]methyl]-1-methylbenzimidazole-5-carbonyl]anilino)propanoateYield 88%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 90 from 1-methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-methoxycarbonylethyl)amide hydrochloride and benzoyl chloride. Yield: 88% of theory, C34H32N6O4 (588.7); Rf value: 0.37 (silica gel; dichloromethane/ethanol=19:1); 1H-NMR spectrum (D6-DMSO): 2.61 (t,2H), 3.54 (s,3H), 3.76 (s,3H), 4.10 (t,2H), 4.61 (d,2H), 6.83 (d,2H), 7.05 to 7.55 (m,12H),8.03 (d,2H), 8.25 (dd,2H), 8.98 (s,1H), 10.48 (s,1H).

Sources & evidence

ORD record
ord-942e1c38554a4eba8c86797266265e49
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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