(2-(4-Methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamine → 1-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(1H-pyrazolo[3,4-b]pyridin-5-yl)urea

HRID 571982ノート

反応式

HRID 571982 の反応式
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([NH:10][C:11](=[O:19])OC3C=CC=CC=3)[CH:9]=[C:4]2[CH:3]=[N:2]1.[CH3:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]2[C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=[C:29]([C:35]([F:38])([F:37])[F:36])[N:28]=2)[CH2:23][CH2:22]1>C(#N)C.CN(C1C=CN=CC=1)C>[CH3:20][CH:21]1[CH2:22][CH2:23][N:24]([C:27]2[C:32]([CH2:33][NH:34][C:11]([NH:10][C:8]3[CH:9]=[C:4]4[CH:3]=[N:2][NH:1][C:5]4=[N:6][CH:7]=3)=[O:19])=[CH:31][CH:30]=[C:29]([C:35]([F:38])([F:36])[F:37])[N:28]=2)[CH2:25][CH2:26]1

参加物

5

反応物 2

HCID 58873687(2-(4-Methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamineHCID 86676322phenyl 1H-pyrazolo[3,4-b]pyridin-5-ylcarbamate

生成物 1

HCID 712372781-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(1H-pyrazolo[3,4-b]pyridin-5-yl)urea収率 71.5%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

To a solution of phenyl 1H-pyrazolo[3,4-b]pyridin-5-ylcarbamate (C) (84 mg, 0.329 mmol) in acetonitrile was added DMAP (40 mg, 0.329 mmol) and (2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamine (D) (90 mg, 0.329 mmol) at room temperature. The reaction mixture was heated to 50° C. for 15 h. TLC showed complete consumption of starting material. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic part was washed with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude was purified by column chromatography to give pure 1-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(1H-pyrazolo[3,4-b]pyridin-5-yl)urea (example compound 5) (102 mg, 71%).

後処理

  1. customconsumption of starting material
  2. additionThe reaction mixture was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic part was washed with water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by column chromatography

出典と根拠

ORDレコード
ord-8ea548b26fb347db8cbb91ce92d88ae1
出典データセット
uspto-grants-2015_05
特許番号
US09029378B2

反応ノート

読み込み中…