Dimethyl Sulfoxide → [3-(2-Quinolinylmethyloxy)benzyloxy]-3-methylbenzo(b)thiophene-2-carboxamide
반응식
C[C:2]1[C:3]2[CH:13]=[C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]4[CH:33]=[CH:32][C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:25]=4)[CH:17]=3)[CH:11]=[CH:10][C:4]=2SC=1C(O)=O.C(N(CC)CC)C.[OH2:41].N[C:43]1[NH:47]N=NN=1.[CH3:48][S:49]([CH3:51])=O>>[N:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:32]=[CH:33][C:24]=1[CH2:23][O:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][O:14][C:12]1[C:13]2[C:3]([CH3:2])=[C:51]([C:43]([NH2:47])=[O:41])[S:49][C:48]=2[CH:4]=[CH:10][CH:11]=1참가 물질
반응 조건
- 온도
- 60 °C
실험 절차
To a stirred solution of 3-methyl-5-[3-(2-quinolinylmethyloxy)benzyloxy]benzo(b)thiophene-2-carboxylic acid (250 mg, 0.55 mmol) in DMSO (6 ml) at room temperature is added 1,1'-carboxyldiimidazole (178 mg, 1.10 mmol) and the resulting solution is stirred at 60° C. for 1 hour. Triethylamine (153 μL, 1.10 mmol) and 5-aminotetrazole monohydrate (113.2 mg, 1.10 mmol) are added successively and the solution stirred at 60° C. for 16 hours. The reaction mixture is cooled to room temperature and poured over ice-water. The pH is adjusted to 10 and the aqueous layer washed with ether. The pH is then adjusted to 3 and the precipitated material obtained by filtration and washing successively with water, ethanol and methylene chloride. Further drying under vacuum affords N-1H-(5-tetrazolyl)-5-[3-(2-quinolinylmethyloxy)benzyloxy ]-3-methylbenzo(b)thiophene-2-carboxamide (M.P. 220-224° C. (dec)).
후처리
- stirringthe solution stirred at 60° C. for 16 hours
- temperatureThe reaction mixture is cooled to room temperature
- washthe aqueous layer washed with ether
- customthe precipitated material obtained by filtration
- washwashing successively with water, ethanol and methylene chloride
- customFurther drying under vacuum
출처 및 근거
- ORD 기록
- ord-9b37c054f2a6481b9e801d9161fea508
- 출처 데이터셋
- uspto-grants-1991_08
- 특허 번호
- US05041453
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