HCID 178441489, compound → HCID 178441488, compound

HRID 1586832Notes

Reaction equation

HRID 1586832 reaction equation
[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH:26]=[CH:25][CH:24]=[C:23]3[C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[C:18]([N+:32]([O-])=O)[CH:17]=2)[C:8]2=[N:9][CH:10]=[CH:11][C:12]([CH3:13])=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]>[Pd].CO>[NH2:32][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[N:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27]1[NH:31][N:30]=[N:29][N:28]=1)[CH2:15][N:14]1[C:8]2=[N:9][CH:10]=[CH:11][C:12]([CH3:13])=[C:7]2[N:6]=[C:5]1[CH2:1][CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 178441489HCID 178441489, compound

Product 1

HCID 178441488HCID 178441488, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-butyl-7-methyl-3-[3-nitro-4-[2-(1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]-3H-imidazo[4,5-b]pyridine (145 mg), 10% palladium on carbon (30 mg), and methanol (5 ml) was stirred at room temperature for 5 hours under hydrogen atmosphere (4 atom). After vacuum filtration, the filtrate was evaporated in vacuo to give a yellow residue of 3-[3-amino-4-[2-(1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]-2-butyl-7-methyl-3H-imidazo[4,5-b]pyridine (130 mg). This residue was treated with acetic anhydride (1 ml) and pyridine (2 ml) at room temperature for 2 hours. The reaction mixture was evaporated in vacuo and purified by preparative thin layer chromatography (ethyl acetate-acetic acid=19:1) to give a brownish viscous oil (65 ml). To a solution of the oil in ethanol (2 ml) was added a solution of sodium hydrogencarbonate (12.8 mg) in water (1 ml) and the mixture was evaporated in vacuo. The residue was dissolved in water (2 ml) and lyophilized to afford sodium salt of 3-[3-acetamido-4-[2-(1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]-2-butyl-7-methyl-3H-imidazo[4,5-b]pyridine (65 mg) as an amorphous powder.

Workup

  1. filtrationAfter vacuum filtration
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-33083e6ca19348c4a27e61373f25d630
Source dataset
uspto-grants-1993_06
Patent number
US05215994

Reaction notes

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