Water → 2-(3-isoquinolin-3-yl-ureido)-1H-benzoimidazole-4-carboxylic acid methyl ester

HRID 1910139

Reaction equation

HRID 1910139 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([NH2:14])[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].C1N=CN([C:20]([N:22]2[CH:26]=[N:25][CH:24]=[CH:23]2)=[O:21])C=1.C1C2[C:31](=[CH:32][CH:33]=[CH:34]C=2)[CH:30]=[C:29](N)N=1.O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([NH:14][C:20]([NH:22][C:26]3[N:25]=[CH:24][C:23]4[C:33]([CH:34]=3)=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:21])[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 311869Isoquinolin-3-AmineHCID 24730367methyl 2-amino-1H-benzo[d]imidazole-4-carboxylate2×

Product 1

HCID 669403712-(3-isoquinolin-3-yl-ureido)-1H-benzoimidazole-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirring mixture of 1.0 g (5.2 mmol) of 2-amino-3H-benzoimidazole-4-carboxylic acid methyl ester (Intermediate A) and 0.86 g (5.2 mmol) of CDI in 3.0 mL of DMF was added 0.75 g (5.2 mmol) of Isoquinolin-3-ylamine. The reaction mixture was heated at 60° C. for 30 min, and then cooled to room temperature. 5.0 mL of water was added. The resulting solid was filtered washed with water (10 ml) and ether (10 mL), and dried to provide the 2-(3-isoquinolin-3-yl-ureido)-1H-benzoimidazole-4-carboxylic acid methyl ester as a solid which was hydrolyzed as described in general procedure B to provide 0.75 g (40%) of 2-(3-isoquinolin-3-yl-ureido)-1H-benzoimidazole-4-carboxylic acid. LCMS: 348 (M+1)+.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe resulting solid was filtered
  3. washwashed with water (10 ml) and ether (10 mL)
  4. customdried

Sources & evidence

ORD record
ord-d1acc2a7670640099f4c19a9e43e2ac9
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Linked notes

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