Sodium Hydroxide → 2-[1,4]diazepan-1-yl-1-[2-(5-methyl-tetrazol-1-yl)-ethyl]-1H-benzoimidazole

HRID 2230721Notes

Reaction equation

HRID 2230721 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:19]([CH2:20][CH2:21][N:22]3[C:26]([CH3:27])=[N:25][N:24]=[N:23]3)[C:18]3[CH:28]=[CH:29][CH:30]=[CH:31][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.I.[OH-].[Na+]>C(O)C>[N:11]1([C:15]2[N:19]([CH2:20][CH2:21][N:22]3[C:26]([CH3:27])=[N:25][N:24]=[N:23]3)[C:18]3[CH:28]=[CH:29][CH:30]=[CH:31][C:17]=3[N:16]=2)[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24841Hydrogen iodideHCID 701476184-{1-[2-(5-methyl-tetrazol-1-yl)-ethyl]-1H-benzoimidazol-2-yl}-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 184644662-[1,4]diazepan-1-yl-1-[2-(5-methyl-tetrazol-1-yl)-ethyl]-1H-benzoimidazoleYield 84.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Reflux 4-{1-[2-(5-methyl-tetrazol-1-yl)-ethyl]-1H-benzoimidazol-2-yl}-[1,4]diazepane-1-carboxylic acid tert-butyl ester (0.42 g, 0.98 mmol) in ethanol (15 mL) with 57% hydroiodic acid (5 mL) for one hour. Cool, treat with sodium hydroxide solution (final pH 13) and extract with dichloromethane (10×50 mL). Dry the combined organic phases (Na2SO4), filter and concentrate the filtrate in vacuo to afford 2-[1,4]diazepan-1-yl-1-[2-(5-methyl-tetrazol-1-yl)-ethyl]-1H-benzoimidazole (0.27 g), Rf=0.60 (silica gel, dichloromethane:methanol:ammonium hydroxide solution, 80:20:0.2).

Workup

  1. temperatureCool
  2. extractionextract with dichloromethane (10×50 mL)
  3. dry with materialDry the combined organic phases (Na2SO4)
  4. filtrationfilter
  5. concentrationconcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-c8f814e5d5724e3595efe880f4c1ff4e
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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