반응식
F[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:10][C:9]=2[CH3:18])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:27](OC1C=CC=CC=1)=[O:28].[Br:36][C:37]1[S:41][C:40]([NH2:42])=[N:39][CH:38]=1.[CH3:43]S(O)(=O)=O.[OH2:48]>C(#N)C>[Br:36][C:37]1[S:41][C:40]([NH:42][C:43]([NH:17][S:14]([C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:6]=[N:7][C:2]([O:28][CH3:27])=[CH:3][CH:4]=3)=[C:9]([CH3:18])[CH:10]=2)(=[O:16])=[O:15])=[O:48])=[N:39][CH:38]=1참가 물질
반응물 6
생성물 1
시약·촉매·용매 1
반응 조건
- 온도
- 60 °C
실험 절차
To a solution of 4-(6-fluoro-pyridin-3-yl)-3-methyl-benzenesulfonamide (4.2 g, 16 mmol) and triethylamine (5.1 ml, 36.8 mmol, 2.3 equiv.) in 130 ml acetonitrile was added dropwise at 0° C. phenyl chloroformate (2.4 ml, 19.2 mmol, 1.2 equiv.) After stirring the solution for one hour at room temp., 5-bromo-thiazol-2-ylamine (4.3 g, 24 mmol, 1.5 equiv.) is added in one portion. The mixture was warmed to 60° C., then methanesulfonic acid (1.5 ml, 24 mmol, 1.5 equiv.) was added and the reaction mixture was stirred for one hour at 60° C. After cooling to room temp., the mixture was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium-dihydrate, filtered and evaporated. The crude product was purified on silica-gel with ethyl acetate/n-heptane to give 2.67 g of the title compound as a light brown solid. MS (ES): m/e 470.7 (M−H)
후처리
- stirringthe reaction mixture was stirred for one hour at 60° C
- temperatureAfter cooling to room temp.
- extractionextracted with ethyl acetate
- washThe combined organic extracts were washed with brine
- dry with materialdried over magnesium-dihydrate
- filtrationfiltered
- customevaporated
- customThe crude product was purified on silica-gel with ethyl acetate/n-heptane
출처 및 근거
- ORD 기록
- ord-720dda439c0149b5952041bdbac68339
- 출처 데이터셋
- uspto-grants-2011_01
- 특허 번호
- US07868030B2
연결된 노트
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