1-Pentanesulfonamide → 1-(Isoquinolin-3-ylmethyl)-2-methyl-6-(1-pentane-sulfonylcarbamoyl)benzimidazole

HRID 2229459

반응식

HRID 2229459 반응식
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[C:10]([CH3:12])[N:9]([CH2:13][C:14]3[N:15]=[CH:16][C:17]4[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:8]=2[CH:24]=1)(O)=[O:2].[CH2:25]([S:30]([NH2:33])(=[O:32])=[O:31])[CH2:26][CH2:27][CH2:28][CH3:29]>CN(C)C=O>[CH:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[C:14]([CH2:13][N:9]2[C:8]3[CH:24]=[C:4]([C:1](=[O:2])[NH:33][S:30]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])(=[O:32])=[O:31])[CH:5]=[CH:6][C:7]=3[N:11]=[C:10]2[CH3:12])[N:15]=1

참가 물질

4

반응물 2

HCID 109206961-PentanesulfonamideHCID 120517556-Carboxy-1-(isoquinolin-3-ylmethyl)-2-methylbenzimidazole

생성물 1

HCID 98465941-(Isoquinolin-3-ylmethyl)-2-methyl-6-(1-pentane-sulfonylcarbamoyl)benzimidazole수율 24.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N,N′-carbonyldiimidazole (0.324 g) was added to a solution of 6-carboxy-1-(isoquinolin-3-ylmethyl)-2-methylbenzimidazole (0.413 g) as obtained in Production Example 5 in N,N-dimethylformamide (10 ml) all at once and the mixture was stirred at room temperature for 1.5 hour. Then, 1-pentanesulfonamide (0.302 g) and diazabicyclo-undecene (0.304 g) were added thereto, and the resulting mixture was stirred at 100° C. for 6.5 hour. The reaction solution was concentrated, brine was added to the concentrate, and the mixture was extracted with chloroform. The organic layer was concentrated and the residue was purified by silica gel column chromatography (eluate: methanol/chloroform=1/19) followed by recrystallization from hexane/ethyl acetate (2/3) to yield the desired compound, 1-(isoquinolin-3-ylmethyl)-2-methyl-6-(1-pentanesulfonyl-carbamoyl)benzimidazole (13) (0.142 g).

후처리

  1. stirringthe resulting mixture was stirred at 100° C. for 6.5 hour
  2. concentrationThe reaction solution was concentrated
  3. additionbrine was added to the concentrate
  4. extractionthe mixture was extracted with chloroform
  5. concentrationThe organic layer was concentrated
  6. customthe residue was purified by silica gel column chromatography (eluate: methanol/chloroform=1/19)
  7. customfollowed by recrystallization from hexane/ethyl acetate (2/3)

출처 및 근거

ORD 기록
ord-2c97d0e2135741fa895f5966314f5042
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06420409B1

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