Tetrahydrofuran → HCID 178504718, 화합물

HRID 25356

반응식

HRID 25356 반응식
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11](Cl)(=[O:13])=[O:12])(=[O:4])=[O:3].O1CCCC1.[NH2:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][N:25]=[C:24]2[Cl:30].C(N(CC)CC)C>O>[Cl:30][C:24]1[C:23]2[C:27](=[CH:28][CH:29]=[C:21]([NH:20][S:11]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[S:2]([CH3:1])(=[O:4])=[O:3])(=[O:13])=[O:12])[CH:22]=2)[NH:26][N:25]=1

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran2회HCID 8471TriethylamineHCID 27351782-Methanesulfonylbenzene-1-sulfonyl chlorideHCID 178507360HCID 178507360, 화합물

생성물 1

HCID 178504718HCID 178504718, 화합물수율 9.9%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

N-(3-Chloro-1H-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide can be obtained in the following way: a solution of 0.36 g of 2-methylsulfonylbenzenesulfonyl chloride and of 3.6 ml of tetrahydrofuran is added dropwise to a solution, cooled to 0° C., of 0.22 g of 5-amino-3-chloro-1H-indazole, of 15 ml of tetrahydrofuran and of 0.37 ml of triethylamine. After reacting for 30 minutes at a temperature in the region of 0° C. and 18 hours at a temperature in the region of 20° C., 30 ml of distilled water are added to the reaction medium. The medium is extracted with 30 ml and 15 ml of ethyl acetate. The organic phase is subsequently dried over magnesium sulfate, filtered and concentrated by evaporation under reduced pressure. The residue thus obtained is purified by chromatography on a silica column with a dichloromethane/methanol (99/1 by volume) mixture as eluent. The solid thus obtained is recrystallized from 45 ml of isopropanol. After drying under reduced pressure at 60° C., 0.05 g of N-(3-chloro-1H-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide is thus obtained in the form of a white solid melting above 260° C. (analysis C14H12ClN3O4S2 % calculated C, 43.58; H, 3.13; Cl, 9.19; N, 10.89; O, 16.59; S, 16.62. % found C, 43.72; H, 2.88; Cl, 7.94; N, 10.63; S, 16.80).

후처리

  1. additionare added to the reaction medium
  2. extractionThe medium is extracted with 30 ml and 15 ml of ethyl acetate
  3. dry with materialThe organic phase is subsequently dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe residue thus obtained
  7. customis purified by chromatography on a silica column with a dichloromethane/methanol (99/1 by volume) mixture as eluent
  8. customThe solid thus obtained
  9. customis recrystallized from 45 ml of isopropanol
  10. customAfter drying under reduced pressure at 60° C.

출처 및 근거

ORD 기록
ord-7aa3391bca8a45dcb855ef7212c14f2b
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858638B2

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