HCID 89485810, compound → HCID 89492432, compound

HRID 1469393Notes

Reaction equation

HRID 1469393 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:19]3[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH:24]=3)=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[N:12]=2)=[CH:4][CH:3]=1.[H][H]>CC(O)=O.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]([CH:19]3[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24]3)=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 89485810HCID 89485810, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 89492432HCID 89492432, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of tert-butyl 4-[2-(4-fluorophenyl)-4-(pyridin-2-yl)-1,3-oxazol-5-yl]-3,6-dihydropyridine-1(2H)-carboxylate (0.2 g, 0.475 mmol) and Pd/C (0.10 g, 10%, 0.095 mmol) in AcOH (20 ml) was hydrogenated on a shaker at 45 psi hydrogen for 2 days. Then the catalyst was filtered off, and the filtrate was concentrated. The resulting residue was purified by reverse phase HPLC to give the title compound. LC-MS m/e 424.25 [M+1]+.

Workup

  1. filtrationThen the catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-3b4ad15fb7ad446d896fa4675bf702d6
Source dataset
uspto-grants-2015_04
Patent number
US09006268B2

Reaction notes

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