N-Cyclopropyl-2,6-bis[(1E)-3-methoxyprop-1-en-1-yl]isonicotinamide → HCID 66760962, compound

HRID 561835Notes

Reaction equation

HRID 561835 reaction equation
[CH:1]1([NH:4][C:5](=[O:22])[C:6]2[CH:11]=[C:10](/[CH:12]=[CH:13]/[CH2:14][O:15][CH3:16])[N:9]=[C:8](/[CH:17]=[CH:18]/[CH2:19][O:20][CH3:21])[CH:7]=2)[CH2:3][CH2:2]1>CCOC(C)=O.[Pd]>[CH:1]1([NH:4][C:5](=[O:22])[C:6]2[CH:7]=[C:8]([CH2:17][CH2:18][CH2:19][O:20][CH3:21])[N:9]=[C:10]([CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:11]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 66761510N-Cyclopropyl-2,6-bis[(1E)-3-methoxyprop-1-en-1-yl]isonicotinamide

Product 1

HCID 66760962HCID 66760962, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-cyclopropyl-2,6-bis[(1E)-3-methoxyprop-1-en-1-yl]isonicotinamide from the previous step (1 eq.) in EtOAc (0.2 M) was added palladium (10% w/w over activated carbon, 40% loading). The reaction vessel was evacuated and back-filled with hydrogen. The reaction suspension was then stirred under a balloon atmosphere of hydrogen for 24 h. The reaction was quenched with CH2Cl2, filtered through celite and the insolubles washed further with EtOAc. Concentration of the filtrate in vacuo and purification of the crude product thus obtained by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc→1:4 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Workup

  1. customThe reaction vessel was evacuated
  2. additionback-filled with hydrogen
  3. customThe reaction was quenched with CH2Cl2
  4. filtrationfiltered through celite
  5. washthe insolubles washed further with EtOAc
  6. customConcentration of the filtrate in vacuo and purification of the crude product
  7. customthus obtained by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc→1:4 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-6c93b0d89eb44c24ab3624c7084f2257
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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