3-{[(1S)-1-methylpropyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide → HCID 59127175, compound

HRID 1175879Notes

Reaction equation

HRID 1175879 reaction equation
[CH3:1][C@H:2]([O:5][C:6]1[CH:7]=[C:8]([CH:18]=[C:19]([O:21]CC2C=CC=CC=2)[CH:20]=1)[C:9]([NH:11][C:12]1[CH:16]=[CH:15][N:14]([CH3:17])[N:13]=1)=[O:10])[CH2:3][CH3:4]>C1COCC1.C(O)C.[Pd]>[OH:21][C:19]1[CH:18]=[C:8]([CH:7]=[C:6]([O:5][C@@H:2]([CH3:1])[CH2:3][CH3:4])[CH:20]=1)[C:9]([NH:11][C:12]1[CH:16]=[CH:15][N:14]([CH3:17])[N:13]=1)=[O:10]

Participants

5

Reactant 1

HCID 536296373-{[(1S)-1-methylpropyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide

Product 1

HCID 59127175HCID 59127175, compoundYield 99.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-{[(1S)-1-methylpropyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide (900 mg) in THF (5 mL) and ethanol (5 mL) containing 10% palladium on carbon was stirred under an atmosphere of hydrogen overnight. The palladium on carbon was removed by filtration and the filtrate evaporated under reduced pressure to give the required compound as a white solid (683 mg). 1H NMR δ (CDCl3): 0.95 (t, 3H), 1.27 (d, 3H), 1.54-1.80 (m, 2H), 3.79 (s, 3H), 4.31 (q, 1H), 6.57 (t, 1H), 6.81 (d, 1H), 6.96 (s, 1H), 6.98 (s, 1H), 7.30 (s, 1H), 7.57 (s, 1H), 8.84 (s, 1H); m/z 290 (M+H)+

Workup

  1. customThe palladium on carbon was removed by filtration
  2. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-9e137978bf1a4b6fb95647a05475c3e0
Source dataset
uspto-grants-2010_11
Patent number
US07842694B2

Reaction notes

Loading…