HCID 54755721, compound → HCID 71280872, compound

HRID 335057Notes

Reaction equation

HRID 335057 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][C:9]([C:11]1[CH:20]=[C:19]([CH2:21][C:22]2[CH:23]=[N:24][C:25]([CH:28]=[CH2:29])=[CH:26][CH:27]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]=1[O:30][CH3:31])=[O:10]>CO.[Pd]>[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][C:9]([C:11]1[CH:20]=[C:19]([CH2:21][C:22]2[CH:23]=[N:24][C:25]([CH2:28][CH3:29])=[CH:26][CH:27]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]=1[O:30][CH3:31])=[O:10]

Participants

4

Reactant 1

HCID 54755721HCID 54755721, compound

Product 1

HCID 71280872HCID 71280872, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-[(1S,2S)-2-hydroxycyclohexyl]-1-methoxy-4-[(6-vinylpyridin-3-yl)methyl]-2-naphthamide (0.050 g, 0.12 mmol) in 5 mL of methanol was added palladium on carbon (0.013 mg, 0.12 mmol). The mixture was placed under an atmosphere of hydrogen (1 atm) for 15 hours and was then filtered through a pad of Celite, which was washed with MeOH. The filtrate was concentrated in vacuo to provide the title compound that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 388.1657 for [M+H]+ [Calculated for C23H22N3O3, [M+H]+=388.1656].

Workup

  1. filtrationwas then filtered through a pad of Celite, which
  2. washwas washed with MeOH
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c55544735c7b4356ae79a03df2665988
Source dataset
uspto-grants-2014_11
Patent number
US08883850B2

Reaction notes

Loading…