Hydrochloric Acid → 1-Oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]benzimidazole-8-carboxylic acid

HRID 1521688Notes

Reaction equation

HRID 1521688 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:17]2[CH:18]=[C:19]([C:22]([OH:24])=[O:23])[CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[C:25]([O:27]C)=O.Cl>CO>[O:27]=[C:25]1[C:14]2=[N:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][C:17]=3[N:13]2[CH2:12][CH2:11][CH2:10][NH:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 672365501-(3-aminopropyl)-2-(methoxycarbonyl)-1H-benzimidazole-6-carboxylic acid hydrochloride

Product 1

HCID 672364761-Oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]benzimidazole-8-carboxylic acidYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethylamine (14.3 g, 141.7 mmol) is added to a solution of the crude 1-(3-aminopropyl)-2-(methoxycarbonyl)-1H-benzimidazole-6-carboxylic acid hydrochloride (20 g, 47.2 mmol) in methanol (100 mL) and reaction mixture is refluxed for 1 h. The reaction mixture is cooled and acidified with 1M HCl. The solvent is evaporated and water is added. The resultant solid is collected by filtration and purified by acid-base neutralization using sodium bicarbonate and conc. HCl to afford the title compound (3.4 g, 30%) as a solid.

Workup

  1. temperatureis refluxed for 1 h
  2. temperatureThe reaction mixture is cooled
  3. customThe solvent is evaporated
  4. additionwater is added
  5. filtrationThe resultant solid is collected by filtration
  6. custompurified by acid-base neutralization

Sources & evidence

ORD record
ord-a4fcd7b636bc4b5bb6d05e8621df9465
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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