Piperidine → 2-cyano-3-[4-[[7-(2,2-dimethylpropanoyl)-5-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-b]pyrazin-2-yl]amino]phenyl]-N-ethyl-prop-2-enamide

HRID 716063Notes

Reaction equation

HRID 716063 reaction equation
[CH3:1][C:2]([CH3:32])([CH3:31])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([NH:14][C:15]3[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=3)[N:12]=2)[N:7]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:6]=1)=[O:4].[C:33]([CH2:35][C:36]([NH:38][CH2:39][CH3:40])=[O:37])#[N:34].N1CCCCC1>CO>[C:33]([C:35](=[CH:19][C:18]1[CH:21]=[CH:22][C:15]([NH:14][C:11]2[N:12]=[C:13]3[C:5]([C:3](=[O:4])[C:2]([CH3:32])([CH3:1])[CH3:31])=[CH:6][N:7]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:8]3=[N:9][CH:10]=2)=[CH:16][CH:17]=1)[C:36]([NH:38][CH2:39][CH3:40])=[O:37])#[N:34]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 2703622-Cyano-N-ethylacetamideHCID 867121234-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzaldehyde

Product 1

HCID 779816092-cyano-3-[4-[[7-(2,2-dimethylpropanoyl)-5-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-b]pyrazin-2-yl]amino]phenyl]-N-ethyl-prop-2-enamideYield 96.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 20 ml vial 4-[[7-(2,2-dimethylpropanoyl)-5-(2-trimethylsilylethoxymethyl)-pyrrolo[2,3-b]pyrazin-2-yl]amino]benzaldehyde (30 mg, 0.070 mmol) was dissolved in methanol (5 ml) and 2-cyano-N-ethyl-acetamide (11.38 mg, 0.1000 mmol) and piperdine (0.01 ml, 0.1300 mmol) were added. The reaction mixture was stirred at room temperature for 5 hr. The solvent was evaporated, the residue was loaded on a silica gel column and eluted with CH2Cl2 to MeOH 0-2, 3% to yield 37 mg of 2-cyano-3-[4-[[7-(2,2-dimethylpropanoyl)-5-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-b]pyrazin-2-yl]amino]phenyl]-N-ethyl-prop-2-enamide.

Workup

  1. customThe solvent was evaporated
  2. washeluted with CH2Cl2 to MeOH 0-2, 3%

Sources & evidence

ORD record
ord-219825985af64787a066bf3420cbab8a
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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