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

HRID 1910139

反応式

HRID 1910139 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-d1acc2a7670640099f4c19a9e43e2ac9
出典データセット
uspto-grants-2013_12
特許番号
US08598353B2

関連ノート

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