HCID 66896394, compound → HCID 66896175, compound

HRID 337577Notes

Reaction equation

HRID 337577 reaction equation
[CH:1]1([N:4]([CH2:12][C:13]2[CH:14]=[C:15]([CH:23]=[CH:24][C:25]([O:27][CH3:28])=[O:26])[CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH2:3][CH2:2]1>CCOC(C)=O.[Pd]>[CH:1]1([N:4]([CH2:12][C:13]2[CH:14]=[C:15]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[C:5]([O:7][C:8]([CH3:10])([CH3:11])[CH3:9])=[O:6])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 66896394HCID 66896394, compound

Product 1

HCID 66896175HCID 66896175, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-{8-[(cyclopropyl{[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]-6-quinolinyl}-2-propenoate (1 eq.) from the previous step in EtOAc (0.1 M) was added palladium (10% (w/w) over carbon, 0.1 eq.). The resulting suspension was evacuated and back-filled repeatedly with hydrogen. Finally, the reaction suspension was allowed to stir under a hydrogen-filled balloon atmosphere for 3 h. The reaction was quenched with the addition of dichloromethane and filtered through a bed of celite. The filtrate was then concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a yellow oil.

Workup

  1. customThe resulting suspension was evacuated
  2. additionback-filled repeatedly with hydrogen
  3. additionfilled balloon atmosphere for 3 h
  4. customThe reaction was quenched with the addition of dichloromethane
  5. filtrationfiltered through a bed of celite
  6. concentrationThe filtrate was then concentrated in vacuo
  7. customPurification of the crude product
  8. customthus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record
ord-8a41cf5dac52478295acccaa7f9bc244
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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