2-Cyano-N,N-dimethylacetamide → 2-cyano-N,N-dimethyl-3-(6-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)pyridin-3-yl)acrylamide

HRID 716044Notes

Reaction equation

HRID 716044 reaction equation
[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][N: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].[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:21][C:20]1[CH:19]=[N: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:24][CH:23]=1)[C:36]([N:38]([CH3:40])[CH3:39])=[O:37])#[N:34]

Participants

5

Reactant 3

HCID 2511432-Cyano-N,N-dimethylacetamideHCID 9793820Piperidine, acetateHCID 86712128HCID 86712128, compound

Product 1

HCID 710142952-cyano-N,N-dimethyl-3-(6-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)pyridin-3-yl)acrylamideYield 88.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 50 ml three necked round bottom flask 6-(7-pivaloyl-5-((2-(trimethylsilyl)-ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)-nicotinaldehyde (0.33 g, 0.00072 mole) and 2-cyano-N,N-dimethylacetamide (0.245 g, 0.00218 mole) was taken in ethanol (10 ml). To this reaction mixture, piperidine acetate (3.3 M solution in water) (0.1 ml) was added drop wise at RT. After completion of the addition, reaction mixture was refluxed for 4 hrs. After completion of the reaction, the ethanol was distilled out and water was added to residue. The aqueous layer was extracted with ethyl acetate and organic layers were combined, dried over Na2SO4, filtered and concentrated to afford crude product. The crude compound was purified by triturated with n-pentane (10.0 ml), pentane layer was decanted and solid was dried under vacuum to yield 0.35 g of 2-cyano-N,N-dimethyl-3-(6-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)pyridin-3-yl)acrylamide.

Workup

  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. extractionThe aqueous layer was extracted with ethyl acetate and organic layers
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford crude product
  11. customThe crude compound was purified
  12. customby triturated with n-pentane (10.0 ml), pentane layer
  13. customwas decanted
  14. customsolid was dried under vacuum

Sources & evidence

ORD record
ord-dcc2c1e7086c4eee8414f77f3a5b1caa
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

Loading…