Sodium Bicarbonate → 4-(2-(Methylsulfinyl)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)-N-(3-(trifluoromethyl)phenyl)picolinamide

HRID 1052046ノート

反応式

HRID 1052046 の反応式
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[CH:17]=[C:16]([N:18]3[CH2:26][C:25]4[CH:24]=[N:23][C:22]([S:27][CH3:28])=[N:21][C:20]=4[CH2:19]3)[CH:15]=[CH:14][N:13]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1.S([O-])(O[O-])(=O)=[O:32].[K+].[K+].[S:39](=[O:42])(O)[O-:40].[Na+].[C:44](=O)(O)[O-].[Na+]>O1CCCC1.O>[CH3:28][S:27]([C:22]1[N:23]=[CH:24][C:25]2[CH2:26][N:18]([C:16]3[CH:15]=[CH:14][N:13]=[C:12]([C:10]([NH:9][C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:29])[F:30])[CH:4]=4)=[O:11])[CH:17]=3)[CH2:19][C:20]=2[N:21]=1)=[O:32].[CH3:44][S:39]([C:22]1[N:23]=[CH:24][C:25]2[CH2:26][N:18]([C:16]3[CH:15]=[CH:14][N:13]=[C:12]([C:10]([NH:9][C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:29])([F:1])[F:30])[CH:4]=4)=[O:11])[CH:17]=3)[CH2:19][C:20]=2[N:21]=1)(=[O:42])=[O:40]

参加物

8

反応物 4

HCID 516892Sodium BicarbonateHCID 10313463Potassium peroxymonosulphateHCID 23665763Sodium BisulfiteHCID 866958544-(2-Methylsulfanyl-5,7-dihydro-pyrrolo[3,4-d]pyrimidin-6-yl)-pyridine-2-carboxylic acid (3-trifluoromethyl-phenyl)-amide

生成物 2

HCID 866958324-(2-(Methylsulfinyl)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)-N-(3-(trifluoromethyl)phenyl)picolinamideHCID 866958334-(2-(methylsulfonyl)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)-N-(3-(trifluoromethyl)phenyl)picolinamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A slurry of 4-(2-Methylsulfanyl-5,7-dihydro-pyrrolo[3,4-d]pyrimidin-6-yl)-pyridine-2-carboxylic acid (3-trifluoromethyl-phenyl)-amide (120 mg, 0.28 mmol) and potassium peroxomonosulfate (Oxone®, 184 mg, 0.30 mmol) in tetrahydrofuran (10 mL) and water (4 mL) was stirred at room temperature for 16 hours. To the reaction was added saturated aqueous sodium bisulfite and saturated aqueous sodium bicarbonate to adjust the pH to 7. The mixture was extracted with chloroform. The extract was washed with water, dried (MgSO4), filtered and evaporated. The resulting solid was dissolved in dichloromethane:methanol (19:1), filtered and applied to chromatography on silica gel (12 g) and eluted with dichloromethane:methanol (19:1) and gave the title compound (15 mg, 0.032 mmol) and 4-(2-(methylsulfonyl)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)-N-(3-(trifluoromethyl)phenyl)picolinamide (18 mg, 0.040 mmol).

後処理

  1. extractionThe mixture was extracted with chloroform
  2. washThe extract was washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe resulting solid was dissolved in dichloromethane:methanol (19:1)
  7. filtrationfiltered
  8. washeluted with dichloromethane:methanol (19:1)

出典と根拠

ORDレコード
ord-303be36af7ed4d5fa4129a7e1adbc587
出典データセット
uspto-grants-2016_07
特許番号
US09388176B2

反応ノート

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