HCID 59547844, compound → HCID 59547885, compound

HRID 1946303Notes

Reaction equation

HRID 1946303 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]CC2C=CC=CC=2)=[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>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[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

4

Reactant 1

HCID 59547844HCID 59547844, compound

Product 1

HCID 59547885HCID 59547885, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-[1-({2-chloro-5-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]-2,6-difluorobenzamide (for a preparation see Example 5)(2.44 g, 5.38 mmol) in ethyl acetate (50 ml) was added to 10% palladium on carbon (wet) (0.585 g, 0.275 mmol) under vacuum. The mixture was hydrogenated at ambient temperature for 2 h. A further amount of 10% palladium on carbon wet (0.79 g) was added and the reaction was stirred for a further 2 h. The reaction mixture was filtered using a 10 g celite cartridge. The filtrate was concentrated in vacuo to leave a brown solid (2.01 g). The residue was preabsorbed on florosil and purified on silica (100 g×2) using 0-100% ethyl acetate-cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a white foam (1.24 g); LCMS: (System 4) MH+=364, tRET=2.42 min.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8333177d9cef4917942ed54889671ef1
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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