Piperidine → HCID 71014341, compound

HRID 716061Notes

Reaction equation

HRID 716061 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].[O:33]=[C:34]([N:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)[CH2:35][C:36]#[N:37].N1CCCCC1>CO>[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]=[C:35]([C:34]([N:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)=[O:33])[C:36]#[N:37])=[CH:17][CH:16]=3)[N:12]=2)[N:7]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:28])[CH3:29])[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 8082Piperidine2×HCID 847651-(Cyanoacetyl)piperidine2×HCID 867121234-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzaldehyde

Product 1

HCID 71014341HCID 71014341, compoundYield 59.6%

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 (35 mg, 0.0800 mmol), 3-oxo-3-(1-piperidyl)propanenitrile (18.01 mg, 0.1200 mmol), piperdine (0.02 ml, 0.15 mmol) and 3-oxo-3-(1-piperidyl)propanenitrile (18.01 mg, 0.12 mmol), were taken in methanol (5 ml). To this reaction mixture, piperdine (0.02 ml, 0.15 mmol) was added drop wise at RT. After completion of the addition, the reaction mixture was stirred for 5 hrs. Ethanol was evaporated, the residue was loaded on silica gel column and elution with CH2Cl2 to MeOH 0-2, 3% yielded 28 mg of 3-[4-[[7-(2,2-dimethylpropanoyl)-5-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-b]pyrazin-2-yl]amino]phenyl]-2-(piperidine-1-carbonyl)prop-2-enenitrile.

Workup

  1. additionAfter completion of the addition
  2. customEthanol was evaporated
  3. washthe residue was loaded on silica gel column and elution with CH2Cl2 to MeOH 0-2, 3%

Sources & evidence

ORD record
ord-ff5e5a6d63bc4465a16f8a8137e973f2
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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