Hydrochloric Acid → 1-Methyl-2-[N-(4-amidinophenyl)-aminomethyl]-benzimidazol-5-yl-carboxylicacid-N-phenyl-N-(2-ethoxycarbonylethyl)-amide-hydrochloride

HRID 2288359Notes

Reaction equation

HRID 2288359 reaction equation
[C:1]1([N:7]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:8]([C:10]2[CH:29]=[CH:28][C:13]3[N:14]([CH3:27])[C:15]([CH2:17][NH:18][C:19]4[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=4)=[N:16][C:12]=3[CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[NH4+:41].[NH4+].[ClH:43]>>[ClH:43].[C:1]1([N:7]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:8]([C:10]2[CH:29]=[CH:28][C:13]3[N:14]([CH3:27])[C:15]([CH2:17][NH:18][C:19]4[CH:24]=[CH:23][C:22]([C:25](=[NH:41])[NH2:26])=[CH:21][CH:20]=4)=[N:16][C:12]=3[CH:11]=2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 517111Ammonium CarbonateHCID 184125221-methyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

Product 1

HCID 184125531-Methyl-2-[N-(4-amidinophenyl)-aminomethyl]-benzimidazol-5-yl-carboxylicacid-N-phenyl-N-(2-ethoxycarbonylethyl)-amide-hydrochloride

Procedure

1.2 g (2.49 mMol) of 1-methyl-2-[N-(4-cyanophenyl)-aminomethyl]-benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)-amide were stirred in 100 ml of saturated ethanolic hydrochloric acid for 6 hours at room temperature. Then the mixture was evaporated to dryness in vacuo, the residue was dissolved in 100 ml of ethanol, mixed with 2.5 g (26 mMol) of ammonium carbonate and stirred overnight at room temperature. After distillation of the solvent the crude product thus obtained was purified by column chromatography (100 g silica gel; eluant: dichloromethane/ethanol=4:1). By concentrating the eluates the desired compound was obtained as a white, amorphous solid. Yield: 1.10 g (83% of theory), Rf value: 0.18 (silica gel; dichloromethane/ethanol=4:1) C28H30N6O3 ×HCl (498.6) ##EQU8##

Workup

  1. customThen the mixture was evaporated to dryness in vacuo
  2. dissolutionthe residue was dissolved in 100 ml of ethanol
  3. distillationAfter distillation of the solvent the crude product
  4. customthus obtained
  5. customwas purified by column chromatography (100 g silica gel; eluant: dichloromethane/ethanol=4:1)
  6. concentrationBy concentrating the eluates the desired compound
  7. customwas obtained as a white, amorphous solid

Sources & evidence

ORD record
ord-77ab552e4ec24001a082b3f3e8c031b3
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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