Methanol → 1-benzyl-2-[(isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid

HRID 1910127

반응식

HRID 1910127 반응식
C[O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([NH:14][C:15]([C:17]3[N:18]=[CH:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:16])[N:10]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].CO.[Li+].[OH-]>C1COCC1>[CH2:27]([N:10]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:13]=2[N:12]=[C:11]1[NH:14][C:15]([C:17]1[N:18]=[CH:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:16])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 587244321-benzyl-2-[(isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid methyl ester

생성물 1

HCID 669405361-benzyl-2-[(isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid수율 100%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
65 °C

실험 절차

To a solution of 45 mg (0.12 mmol) of (1-benzyl-2-[(isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid methyl ester (Example 134) in THF (1 mL) was added methanol (1 mL) and 1 N LiOH solution (1 mL). The reaction was heated at 65° C. for 45 min., and the conversion was monitored by TLC. After cooling to room temperature, the organic solvents were removed under reduced pressure, the reaction residue was acidified (pH=2) by addition of 1 N HCl solution. The solid product was collected by filtration and further dried to afford 43 mg (100%) 1-benzyl-2-[(isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid. LCMS: 423 (M+1)+.

후처리

  1. temperatureAfter cooling to room temperature
  2. customthe organic solvents were removed under reduced pressure
  3. additionby addition of 1 N HCl solution
  4. filtrationThe solid product was collected by filtration
  5. customfurther dried

출처 및 근거

ORD 기록
ord-7cbb9355d89b471fa4f175c5e642cfe3
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598353B2

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