2-Cyano-N,N-dimethylacetamide → N-tert-butyl-2-(4-(2-cyano-3-(dimethylamino)-3-oxoprop-1-enyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 716054Notes

Reaction equation

HRID 716054 reaction equation
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH:24]=O)=[CH:20][CH:19]=3)[N:15]=2)[N:10]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:34]([CH2:36][C:37]([N:39]([CH3:41])[CH3:40])=[O:38])#[N:35].C(O)(=O)C.N1CCCCC1>C(O)C>[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([CH:24]=[C:36]([C:34]#[N:35])[C:37]([N:39]([CH3:41])[CH3:40])=[O:38])=[CH:22][CH:23]=3)[N:15]=2)[N:10]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 2511432-Cyano-N,N-dimethylacetamideHCID 9793820Piperidine, acetateHCID 86712130N-tert-butyl-2-(4-formylphenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Product 1

HCID 71014257N-tert-butyl-2-(4-(2-cyano-3-(dimethylamino)-3-oxoprop-1-enyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamideYield 56.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 25 ml three necked round bottom flask, N-tert-butyl-2-(4-formylphenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.022 g, 0.000047 mol) and 2-cyano-N,N-dimethylacetamide (0.021 g, 0.000187 mol) was taken in ethanol (2 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 overnight. After completion of the reaction, the ethanol was distilled out and water was added to the residue. Aqueous was extracted with ethyl acetate, organic layers were combined, dried over Na2SO4, filtered and concentrated to afford crude product which was purified by triturated with n-pentane. The solid was filtered and dried under vacuum to yield 0.015 g of N-tert-butyl-2-(4-(2-cyano-3-(dimethylamino)-3-oxoprop-1-enyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)-methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide.

Workup

  1. additionAfter completion of the addition, reaction mixture
  2. temperaturewas refluxed overnight
  3. customAfter completion of the reaction
  4. distillationthe ethanol was distilled out and water
  5. additionwas added to the residue
  6. extractionAqueous was extracted with ethyl acetate, organic layers
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford crude product which
  11. customwas purified
  12. customby triturated with n-pentane
  13. filtrationThe solid was filtered
  14. customdried under vacuum

Sources & evidence

ORD record
ord-9349a4034ae1412da10492362724ee91
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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