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

HRID 1367868

반응식

HRID 1367868 반응식
[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]

참가 물질

6

반응물 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 311869Isoquinolin-3-AmineHCID 24730367methyl 2-amino-1H-benzo[d]imidazole-4-carboxylate2회

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-1a9b8ec3a5dc4f678d8cec8daf235a2d
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893267B2

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