HCID 19921339, compound → HCID 19921222, compound

HRID 1647887Notes

Reaction equation

HRID 1647887 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]([NH:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[O:15])=[CH:13][C:8]=2[N:7]=[C:6]1[C:23]1[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=1.[H][H]>CO.Cl.[Pd]>[NH2:30][CH2:29][C:26]1[CH:25]=[CH:24][C:23]([C:6]2[N:5]([CH2:4][CH2:3][CH2:2][NH2:1])[C:9]3[CH:10]=[CH:11][C:12]([C:14]([NH:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[O:15])=[CH:13][C:8]=3[N:7]=2)=[CH:28][CH:27]=1

Participants

6

Reactant 2

HCID 19921339HCID 19921339, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19921222HCID 19921222, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

3 g of 1-(3-amino-propyl)-2-(4-cyano-phenyl)-5-[(2-methoxycarbonyl-ethyl)-aminocarbonyl]-benzimidazole are treated in a mixture of 50 ml of methanol and 10 ml of methanolic hydrochloric acid with 5 bars of hydrogen in the presence of 1 g of 10% palladium/charcoal for 20 hours at ambient temperature. After the catalyst has been filtered off the mixture is evaporated to dryness in vacuo and the residue is purified by chromatography on silica gel (eluant:methanol/2N ammonia=5:1.5 to 5:2). Yield: 1.5 g (55% of theory), Rf value: 0.24 (silica gel; methanol/2N ammonia=5:1.5 after developing twice)

Workup

  1. filtrationAfter the catalyst has been filtered off the mixture
  2. customis evaporated to dryness in vacuo
  3. customthe residue is purified by chromatography on silica gel (eluant:methanol/2N ammonia=5:1.5 to 5:2)

Sources & evidence

ORD record
ord-84a4eaaecee540e295ab51eb65360152
Source dataset
uspto-grants-1995_07
Patent number
US05434150

Reaction notes

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