N-[1-({2-Chloro-6-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]-2,6-difluorobenzamide → HCID 59547909, compound

HRID 1946301Notes

Reaction equation

HRID 1946301 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8]CC2C=CC=CC=2)[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>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[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

Participants

4

Reactant 1

HCID 59547897N-[1-({2-Chloro-6-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]-2,6-difluorobenzamide

Product 1

HCID 59547909HCID 59547909, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-[1-({2-chloro-6-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]-2,6-difluorobenzamide (for a preparation see Intermediate 10)(0.148 g, 0.326 mmol) in ethyl acetate (20 ml) was hydrogenated using an H-cube (settings: 20° C., 1 bar, 1 ml/min flow rate) and 5% Pd/C CatCart 30 as the catalyst. The solution was hydrogenated again using an H-cube (settings: 20° C., 1 bar, 1 ml/min flow rate) and 10% Pd/C CatCart 30 as the catalyst. The solvent was removed in vacuo to give the title compound as a colourless gum (70 mg); LCMS: (System 1) MH+=364, tRET=3.14 min.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2732772066ed40a29122958fa3ba6059
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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