Piperidine → HCID 71015365、化合物

HRID 716068ノート

反応式

HRID 716068 の反応式
[C:1]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([NH:16][C:17]3[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=3)[N:14]=2)[N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:8]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[N:33]1([CH2:38][C:39]#[N:40])[CH:37]=[N:36][CH:35]=[N:34]1.N1CCCCC1.C(OCC)(=O)C.CCCCCC>C(O)C>[C:1]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([CH:21]=[C:38]([N:33]4[CH:37]=[N:36][CH:35]=[N:34]4)[C:39]#[N:40])=[CH:23][CH:24]=3)[N:14]=2)[N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:30])[CH3:31])[CH:8]=1)(=[O:6])[C:2]([CH3:3])([CH3:4])[CH3:5]

参加物

6

反応物 4

HCID 8082PiperidineHCID 27648382-(1H-1,2,4-triazol-1-yl)acetonitrileHCID 21226206Ethyl acetate hexaneHCID 867121234-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzaldehyde

生成物 1

HCID 71015365HCID 71015365、化合物収率 43.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

To a 50 ml three necked round bottom flask, 4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)-methyl)-5H-pyrrolo[2,3-b]pyrazine-2-ylamino)benzaldehyde (0.1 g, 0.22 mmole) and 2-(1H-1,2,4-triazol-1-yl)acetonitrile (0.0716 g, 0.66 mmole) was taken in ethanol (5 mL). To this reaction mixture, piperidine (0.2 mL) was added drop wise at RT. After completion of the addition, the reaction mass was refluxed for 16 hrs and the completion of the reaction was monitored on TLC using ethyl acetate:hexane (5:5) as a mobile phase. After completion of the reaction, ethanol was distilled out and water was added to residue. Aqueous was extracted with ethyl acetate, organic layers were combined, dried over Na2SO4, filtered and concentrated to afford crude product. The crude compound was purified using column purification by eluting the compound with 40% ethyl acetate in hexanes triturated with n-pentane, pentane layer was decanted and solid was dried under vacuum to yield 0.052 g of 3-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)-2-(1H-1,2,4-triazol-1-yl)acrylonitrile.

後処理

  1. additionAfter completion of the addition
  2. temperaturethe reaction mass was refluxed for 16 hrs
  3. distillationwas distilled out and water
  4. additionwas added to residue
  5. extractionAqueous was extracted with ethyl acetate, organic layers
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford crude product
  10. customThe crude compound was purified
  11. customcolumn purification
  12. washby eluting the compound with 40% ethyl acetate in hexanes
  13. customtriturated with n-pentane, pentane layer
  14. customwas decanted
  15. customsolid was dried under vacuum

出典と根拠

ORDレコード
ord-d1c86bb256144f508255fbadcd757ee6
出典データセット
uspto-grants-2015_11
特許番号
US09187487B2

反応ノート

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