N-[1-({2-Chloro-4-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]-2,6-difluorobenzamide → N-{1-[(2-Chloro-4-hydroxyphenyl)methyl]-1H-pyrazol-3-yl}-2,6-difluorobenzamide

HRID 1946371Notes

Reaction equation

HRID 1946371 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8]CC2C=CC=CC=2)[CH:5]=[CH:4][C:3]=1[CH2:16][N:17]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:32])[C:24]2[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=2[F:31])=[N:18]1>CO.ClCCl.[Pd]>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:16][N:17]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:32])[C:24]2[C:25]([F:31])=[CH:26][CH:27]=[CH:28][C:29]=2[F:30])=[N:18]1

Participants

5

Reactant 1

HCID 59547945N-[1-({2-Chloro-4-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]-2,6-difluorobenzamide

Product 1

HCID 59547950N-{1-[(2-Chloro-4-hydroxyphenyl)methyl]-1H-pyrazol-3-yl}-2,6-difluorobenzamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of {N-[1-({2-chloro-4-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]-2,6-difluorobenzamide (for a preparation see Example 30)(0.731 g, 1.61 mmol) in methanol (35 ml) was hydrogenated using the H-cube (settings: ambient, 1 bar, 1 ml/min flow rate) and 10% Pd/C CatCart 30 as the catalyst. The solvent was removed in vacuo to leave an oil. The residue was loaded in dichloromethane and purified on silica (100 g) using 0-100% ethyl acetate-cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a colourless oil (0.331 g); LCMS: (System 4) MH+=364, tRET=2.36 min.

Workup

  1. customThe solvent was removed in vacuo
  2. customto leave an oil
  3. custompurified on silica (100 g)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-beca40f43ef74cc9a2dfbbaa34f85b6d
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

Loading…