Ammonium Acetate → 2-isoquinolin-3-yl-1H-benzoimidazole-4-carboxylic acid

HRID 1844944Notes

Reaction equation

HRID 1844944 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]([C:13]2[N:14]=[CH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)=O)[C:5]=1[NH2:23].C([O-])(C)=O.[NH4+]>CC(O)=O>[CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[C:13]([C:11]2[NH:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([C:3]([OH:2])=[O:24])[C:5]=3[N:23]=2)[N:14]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 669403142-Amino-3-[(isoquinoline-3-carbonyl)-amino]-benzoic acid methyl ester

Product 1

HCID 669406062-isoquinolin-3-yl-1H-benzoimidazole-4-carboxylic acidYield 55%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of the above crude product 2-amino-3-[(isoquinoline-3-carbonyl)-amino]-benzoic acid methyl ester in AcOH (25 mL) was added AcONH4 (16 g). The reaction mixture was refluxed for 3 h. After removal of AcOH under vacuum, the reaction mixture was washed with water (150 mL) The crude solid product 2-isoquinolin-3-yl-1H-benzoimidazole-4-carboxylic acid methyl ester was collected after filtration. LCMS: 304 (M+1)+. This product was hydrolyzed according to the general procedure C to provide 2-isoquinolin-3-yl-1H-benzoimidazole-4-carboxylic acid (1.6 g, 55% yield over three steps). LCMS: 290 (M+1)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customAfter removal of AcOH under vacuum
  3. washthe reaction mixture was washed with water (150 mL) The crude solid product 2-isoquinolin-3-yl-1H-benzoimidazole-4-carboxylic acid methyl ester
  4. customwas collected
  5. filtrationafter filtration

Sources & evidence

ORD record
ord-7c93dae8daac4e52bde22355ac7019bb
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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