Acetonitrile → HCID 71143552、化合物

HRID 571461ノート

反応式

HRID 571461 の反応式
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[CH:10][N:9]=[C:8]3[N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][C:7]=23)[CH:3]=[N:2]1.[C:23]([CH:25]=[C:26]1[CH2:29][N:28]([C:30]2[CH:41]=[CH:40][C:33]([C:34]([NH:36][CH:37]([CH3:39])[CH3:38])=[O:35])=[CH:32][CH:31]=2)[CH2:27]1)#[N:24].N12CCCN=C1CCCCC2.C(#N)C>>[C:23]([CH2:25][C:26]1([N:1]2[CH:5]=[C:4]([C:6]3[CH:11]=[CH:10][N:9]=[C:8]4[N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][C:7]=34)[CH:3]=[N:2]2)[CH2:29][N:28]([C:30]2[CH:41]=[CH:40][C:33]([C:34]([NH:36][CH:37]([CH3:38])[CH3:39])=[O:35])=[CH:32][CH:31]=2)[CH2:27]1)#[N:24]

参加物

5

反応物 4

HCID 6342AcetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 574775784-(1H-Pyrazol-4-yl)-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridineHCID 71143653HCID 71143653、化合物

生成物 1

HCID 71143552HCID 71143552、化合物収率 100.3%

反応条件

温度
50 °C

実験手順

A mixture of 4-(1H-pyrazol-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine (0.811 g, 2.58 mmol), 4-[3-(cyanomethylene)azetidin-1-yl]-N-isopropylbenzamide (0.625 g, 2.45 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (190 μL, 1.3 mmol) in acetonitrile (8 mL, 200 mmol) was heated at 50° C. for 1 hour. After cooling, the solvent was removed under reduced pressure. The residue was diluted with dichloromethylene, neutralized with 0.5 N HCl aqueous solution to about pH 7. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford the desired product (1.40 g, 84.3%), which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=570.3.

後処理

  1. temperatureAfter cooling
  2. customthe solvent was removed under reduced pressure
  3. additionThe residue was diluted with dichloromethylene
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-768ca25edefc4fcba03929ab1aa0d500
出典データセット
uspto-grants-2015_05
特許番号
US09023840B2

反応ノート

読み込み中…