2-Cyano-N,N-dimethylacetamide → 2-cyano-N,N-dimethyl-3-(5-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)-methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl-amino)pyridin-2-yl)acrylamide

HRID 716049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 716049
[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:23]=O)=[N:21][CH:22]=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].[C:33]([CH2:35][C:36]([N:38]([CH3:40])[CH3:39])=[O:37])#[N:34].C(O)(=O)C.N1CCCCC1>C(O)C>[C:33]([C:35](=[CH:23][C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:13]2[N:14]=[C:15]3[C:7]([C:1](=[O:6])[C:2]([CH3:5])([CH3:3])[CH3:4])=[CH:8][N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:10]3=[N:11][CH:12]=2)=[CH:22][N:21]=1)[C:36]([N:38]([CH3:40])[CH3:39])=[O:37])#[N:34]

Komponenten

5

Edukt 3

HCID 2511432-Cyano-N,N-dimethylacetamideHCID 9793820Piperidine, acetateHCID 867121295-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)picolinaldehyde

Produkt 1

HCID 779816222-cyano-N,N-dimethyl-3-(5-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)-methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl-amino)pyridin-2-yl)acrylamideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

In a 50 ml three necked round bottom flask, 5-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)picolinaldehyde (0.17 g, 0.00037 mole) and 2-cyano-N,N-dimethylacetamide (0.084 g, 0.00075 mole) was taken in ethanol (5 ml). Piperidine acetate (3.3 M solution in water) (0.2 ml) was added dropwise at RT. After completion of the addition, reaction mixture was refluxed for 4 hrs and after completion of the reaction, the ethanol was distilled out and water was added to residue. Aqueous layer was extracted with ethyl acetate, organic layers were combined, dried over Na2SO4, filtered and concentrated to afford crude product. The crude compound was triturated with n-pentane, the pentane layer was decanted and solid was dried under vacuum to yield 0.152 g of 2-cyano-N,N-dimethyl-3-(5-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)-methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl-amino)pyridin-2-yl)acrylamide which was converted to the title compound as described in Example 8 above.

Aufarbeitung

  1. additionAfter completion of the addition, reaction mixture
  2. temperaturewas refluxed for 4 hrs
  3. customafter completion of the reaction
  4. distillationthe ethanol was distilled out and water
  5. additionwas added to residue
  6. extractionAqueous layer was extracted with ethyl acetate, organic layers
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford crude product
  11. customThe crude compound was triturated with n-pentane
  12. customthe pentane layer was decanted
  13. customsolid was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ead616fc2bf649d1aafbb8925b5d1ebc
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187487B2

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