Hydrochloric Acid → 2-butyl-3-[4-[4-ethoxycarbonyl-2-(1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]-7-methyl-3H-imidazo[4,5-b]pyridine

HRID 1586836Notes

Reaction equation

HRID 1586836 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]=[C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:24]=[C:23]3[C:32]3[N:36](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:35]=[N:34][N:33]=3)=[CH:18][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].Cl>CO>[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([N:22]3[CH:26]=[C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:24]=[C:23]3[C:32]3[NH:36][N:35]=[N:34][N:33]=3)=[CH:20][CH:21]=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]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 197592572-butyl-3-[4-[4-ethoxycarbonyl-2-(1-trityl-1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]-7-methyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 1784414912-butyl-3-[4-[4-ethoxycarbonyl-2-(1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]-7-methyl-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-butyl-3-[4-[4-ethoxycarbonyl-2-(1-trityl-1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]-7-methyl-3H-imidazo[4,5-b]pyridine (115 mg), conc. hydrochloric acid (0.25 ml) and methanol (20 ml) was stirred for 2 hours and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography to give 2-butyl-3-[4-[4-ethoxycarbonyl-2-(1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]-7-methyl-3H-imidazo[4,5-b]pyridine [53 mg) as a colorless viscous oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-d2febcaca8a841419e532343dc48a578
Source dataset
uspto-grants-1993_06
Patent number
US05215994

Reaction notes

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