HCID 19921222, compound → HCID 67805268, compound

HRID 1647896Notes

Reaction equation

HRID 1647896 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([CH2:14][CH2:15][CH2:16][NH2:17])[C:12]3[CH:18]=[CH:19][C:20]([C:22]([NH:24][CH2:25][CH2:26][C:27]([O:29]C)=[O:28])=[O:23])=[CH:21][C:11]=3[N:10]=2)=[CH:5][CH:4]=1>Br>[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:13]([CH2:14][CH2:15][CH2:16][NH2:17])[C:12]3[CH:18]=[CH:19][C:20]([C:22]([NH:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:23])=[CH:21][C:11]=3[N:10]=2)=[CH:7][CH:8]=1.[C:27]([OH:29])(=[O:28])[CH3:26]

Participants

3

Reactant 1

HCID 19921222HCID 19921222, compound

Product 1

HCID 67805268HCID 67805268, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

0.8 g of 2-(4-aminomethyl-phenyl)-1-(3-amino-propyl)-5-[(2-methoxycarbonyl-ethyl)-aminocarbonyl]-benzimidazole are left to stand for 20 hours at ambient temperature in 10 ml of 48% hydrobromic acid. The mixture is concentrated by evaporation in vacuo and the residue is purified by chromatography on silica gel (eluant:n-butanol/glacial acetic acid/water=4:1:1 to 4:2:2). Yield: 0.6 g (67% of theory), Rf value: 0.66 (Reversed Phase Plate RP18; methanol/5% sodium chloride solution/conc. hydrobromic acid=6:10:0.01)

Workup

  1. concentrationThe mixture is concentrated by evaporation in vacuo
  2. customthe residue is purified by chromatography on silica gel (eluant:n-butanol/glacial acetic acid/water=4:1:1 to 4:2:2)

Sources & evidence

ORD record
ord-53afc7a7715946d6aa7dd026bc5129ad
Source dataset
uspto-grants-1995_07
Patent number
US05434150

Reaction notes

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