Trifluoroacetic acid → 3-{1-[4-Difluoromethyl-6-(6-trifluoromethyl-pyridin-3-yl)-pyrimidin-2-yl]-1H-imidazol-4-yl}-benzenesulfonamide

HRID 1962932ノート

反応式

HRID 1962932 の反応式
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:16]=[CH:17][N:18]([C:20]3[N:25]=[C:24]([CH:26]([F:28])[F:27])[CH:23]=[C:22]([C:29]4[CH:30]=[N:31][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:34]=4)[N:21]=3)[CH:19]=2)[CH:10]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[F:28][CH:26]([F:27])[C:24]1[CH:23]=[C:22]([C:29]2[CH:30]=[N:31][C:32]([C:35]([F:38])([F:36])[F:37])=[CH:33][CH:34]=2)[N:21]=[C:20]([N:18]2[CH:19]=[C:15]([C:11]3[CH:10]=[C:9]([S:6]([NH2:5])(=[O:8])=[O:7])[CH:14]=[CH:13][CH:12]=3)[N:16]=[CH:17]2)[N:25]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 673932143-{1-[4-Difluoromethyl-6-(6-trifluoromethyl-pyridin-3-yl)-pyrimidin-2-yl]-1H-imidazol-4-yl}-benzenesulfonic acid tert-butylamide

生成物 1

HCID 673933083-{1-[4-Difluoromethyl-6-(6-trifluoromethyl-pyridin-3-yl)-pyrimidin-2-yl]-1H-imidazol-4-yl}-benzenesulfonamide収率 40.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a cooled and stirred solution of 3-{1-[4-difluoromethyl-6-(6-trifluoromethyl-pyridin-3-yl)-pyrimidin-2-yl]-1H-imidazol-4-yl}-benzenesulfonic acid tert-butylamide (0.06 g) in dichloromethane (2 ml) was added TFA (2 ml) and the reaction mixture was allowed to stir at room temperature for 15 h. The mixture was evaporated to dryness, poured into 2N Na2CO3 solution (25 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine (50 ml), dried (MgSO4) and evaporated. Further purification by column chromatography on silica gel (dichloromethane/MeOH/NH4OH 16:1:0.1) and crystallization (diethyl ether) yielded the title compound as a white solid (0.022 g, 4%). MS (ISP) 497.2 [(M+H)+]; mp 219.5° C.

後処理

  1. temperatureTo a cooled
  2. customThe mixture was evaporated to dryness
  3. additionpoured into 2N Na2CO3 solution (25 ml)
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. washThe combined organic layers were washed with brine (50 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customFurther purification by column chromatography
  9. customon silica gel (dichloromethane/MeOH/NH4OH 16:1:0.1) and crystallization (diethyl ether)

出典と根拠

ORDレコード
ord-01acc741b1c04d9dae7c254485a2d335
出典データセット
uspto-grants-2013_04
特許番号
US08415380B2

反応ノート

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