HCID 58452306, compound → HCID 58452354, compound

HRID 70616Notes

Reaction equation

HRID 70616 reaction equation
[CH:1]1(/[CH:6]=[C:7](/[C:20]2[NH:25][C:24](=[O:26])[C:23]([CH3:27])=[CH:22][CH:21]=2)\[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]3[CH2:19][CH2:18]3)(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>O1CCCC1.CO.[Pd]>[CH:1]1([CH2:6][CH:7]([C:20]2[NH:25][C:24](=[O:26])[C:23]([CH3:27])=[CH:22][CH:21]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]3[CH2:18][CH2:19]3)(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 58452306HCID 58452306, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58452354HCID 58452354, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10% palladium-activated carbon (50 mg) was added to a mixed solution of 6-{(E)-2-cyclopentyl-1-[4-(cyclopropylsulfonyl)phenyl]ethenyl}-3-methylpyridin-2(1H)-one synthesized in Example 1-11 (50 mg) in tetrahydrofuran and methanol (2 mL, 1:1), and the mixture was stirred in a hydrogen gas stream at room temperature for three hours. The reaction solution was filtered through celite, and then the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=1:1→0:1) to give the title compound as a colorless amorphous (33 mg, 60%).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (chloroform:methanol=1:1→0:1)

Sources & evidence

ORD record
ord-2cfaf1fa940a4f2cb408dbf0656f9bbb
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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