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

HRID 748493

反応式

HRID 748493 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
-25 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b418de91e50642878c73ca9e3c004e4e
出典データセット
uspto-grants-2008_07
特許番号
US07399781B2

関連ノート

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