HCID 86588153, compound → HCID 22063714, compound

HRID 1828551Notes

Reaction equation

HRID 1828551 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[N:10]=[C:11]3[CH:25]=[C:24]([CH2:26][CH2:27][C:28]4[S:29][CH:30]=[C:31]([CH:33]([CH3:35])[CH3:34])[N:32]=4)[CH:23]=[CH:22][N:12]3[C:13](=[O:21])[C:14]=2/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18])[CH2:4]1)=[O:2]>C(O)C.[Pd]>[CH:1]([CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[N:10]=[C:11]3[CH:25]=[C:24]([CH2:26][CH2:27][C:28]4[S:29][CH:30]=[C:31]([CH:33]([CH3:35])[CH3:34])[N:32]=4)[CH:23]=[CH:22][N:12]3[C:13](=[O:21])[C:14]=2[CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:4]1)=[O:2]

Participants

4

Reactant 1

HCID 86588153HCID 86588153, compound2×

Product 1

HCID 22063714HCID 22063714, compoundYield 29.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The methyl (E)-3-{2-(3-formylpiperidino)-8-[2-(4-isopropyl-1,3-thiazol-2-yl)-ethyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate (80.9 mg, 0.158 mmol) obtained in (A) was dissolved in ethanol (3 ml), added with 5% palladium/carbon (30 mg) and stirred at 1 atm for 2 days under hydrogen atmosphere. The catalyst was removed by filtration, and the filtrate was concentrated. The resulting residue was purified by preparative TLC (chloroform:methanol=100:2) to obtain the title compound (23.1 mg, 28%).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was purified by preparative TLC (chloroform:methanol=100:2)

Sources & evidence

ORD record
ord-3a47b768fb76431bbeecc347d83bc844
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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