Hydrochloric Acid → 1-Methyl-2-[(4-amidinophenyl)thiomethyl]-benzimidazol-5-yl-carboxylic acid-n-(2-methylpropyl)-n-(2-ethoxycarbonylethyl)-amide-hydrochloride

HRID 50233Notes

Reaction equation

HRID 50233 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11](O)=[O:12])=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:14][S:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=1.[CH3:24][CH:25]([CH3:35])[CH2:26][N-:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].[ClH:36].C(=O)([O-])[O-].[NH4+:41].[NH4+].C(OCC)(=O)C.C(O)C.N>C(O)C>[ClH:36].[CH3:24][CH:25]([CH3:35])[CH2:26][N:27]([CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:11]([C:9]1[CH:8]=[CH:7][C:6]2[N:2]([CH3:1])[C:3]([CH2:14][S:15][C:16]3[CH:21]=[CH:20][C:19]([C:22](=[NH:23])[NH2:41])=[CH:18][CH:17]=3)=[N:4][C:5]=2[CH:10]=1)=[O:12]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 517111Ammonium CarbonateHCID 86587043Ethyl acetate ethanol ammoniaHCID 867555171-Methyl-2-[(4-cyanophenyl)thiomethyl]-benzimidazol-5-yl-carboxylic acidHCID 867555182-methylpropyl-N-(2-ethoxycarbonylethyl)amide

Product 1

HCID 184124631-Methyl-2-[(4-amidinophenyl)thiomethyl]-benzimidazol-5-yl-carboxylic acid-n-(2-methylpropyl)-n-(2-ethoxycarbonylethyl)-amide-hydrochlorideYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared analogously to Example 27 from 1-methyl-2-[(4-cyanophenyl)thiomethyl]benzimidazol-5-yl-carboxylic acid-(N-(2-methylpropyl-N-(2-ethoxycarbonylethyl)amide, ethanolic hydrochloric acid, ethanol, and ammonium carbonate. Yield: 83% of theory, C25H31N6O3S (495.65); Rf value: 0.30 (silica gel; ethyl acetate/ethanol/ammonia=50:45:5); EKA mass spectrum: (M+H)+=496.

Sources & evidence

ORD record
ord-3b0b20561226416d8d6b8cbe908ff7f6
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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