Hydrochloric Acid → 5-fluoro-N-[2-methanesulfonyl-4-(5-methoxy-4-methylthiazol-2-yl)phenyl]-3-methylbenzo[b]thiophene-2-sulfonamide

HRID 748493노트

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HRID 748493 반응식
[CH3:1][S:2]([C:5]1[CH:11]=[C:10]([C:12]2[S:13][C:14]([O:18][CH3:19])=[C:15]([CH3:17])[N:16]=2)[CH:9]=[CH:8][C:6]=1[NH2:7])(=[O:4])=[O:3].[H-].[Na+].Cl[S:23]([C:26]1[S:30][C:29]2[CH:31]=[CH:32][C:33]([F:35])=[CH:34][C:28]=2[C:27]=1[CH3:36])(=[O:25])=[O:24].Cl>CC(N(C)C)=O.C1COCC1>[F:35][C:33]1[CH:32]=[CH:31][C:29]2[S:30][C:26]([S:23]([NH:7][C:6]3[CH:8]=[CH:9][C:10]([C:12]4[S:13][C:14]([O:18][CH3:19])=[C:15]([CH3:17])[N:16]=4)=[CH:11][C:5]=3[S:2]([CH3:1])(=[O:3])=[O:4])(=[O:24])=[O:25])=[C:27]([CH3:36])[C:28]=2[CH:34]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 27745865-Fluoro-3-methylbenzo[b]thiophene-2-sulphonyl chlorideHCID 12148699HCID 12148699, 화합물

생성물 1

HCID 121487005-fluoro-N-[2-methanesulfonyl-4-(5-methoxy-4-methylthiazol-2-yl)phenyl]-3-methylbenzo[b]thiophene-2-sulfonamide수율 70.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 31374Dimethylacetamide용매

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온도
-25 °C

실험 절차

Under an argon atmosphere, 41 mg of 2-methanesulfonyl-4-(5-methoxy-4-methylthiazol-2-yl)aniline was dissolved into a mixed solution of 3 mL of THF and 3 mL of dimethylacetamide. The solution was cooled to −25° C. and 15 mg of sodium hydride (oily, 60%) was added thereto, followed by 10 minutes of stirring at the same temperature. Further, 44 mg of 2-chlorosulfonyl-5-fluoro-3-methylbenzo[b]thiophene was added and the whole was stirred for 2 hours at the same temperature, followed by termination of the reaction with 1 mol/L hydrochloric acid. After the reaction mixture was warmed to room temperature, the mixture was extracted with ethyl acetate-toluene (2/1) and the organic layer was washed with water and saturated brine, successively. After the organic layer was dried over anhydrous sodium sulfate, the solvent was removed by evaporation under reduced pressure and the resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) to obtain 51 mg of the title compound as light yellow powder.

후처리

  1. stirringthe whole was stirred for 2 hours at the same temperature
  2. temperatureAfter the reaction mixture was warmed to room temperature
  3. extractionthe mixture was extracted with ethyl acetate-toluene (2/1)
  4. washthe organic layer was washed with water and saturated brine
  5. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed by evaporation under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1)

출처 및 근거

ORD 기록
ord-b418de91e50642878c73ca9e3c004e4e
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399781B2

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