Water → 2,6-Difluoro-N-{1-[(4-hydroxy-2-methylphenyl)methyl]-1H-pyrazol-3-yl}benzamide

HRID 1946389Notes

Reaction equation

HRID 1946389 reaction equation
O.CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C.[F:29][C:30]1[CH:59]=[CH:58][CH:57]=[C:56]([F:60])[C:31]=1[C:32]([NH:34][C:35]1[CH:39]=[CH:38][N:37]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([O:47]CC3C=CC=CC=3)=[CH:43][C:42]=2[CH3:55])[N:36]=1)=[O:33]>[Pd].C(OCC)(=O)C>[F:29][C:30]1[CH:59]=[CH:58][CH:57]=[C:56]([F:60])[C:31]=1[C:32]([NH:34][C:35]1[CH:39]=[CH:38][N:37]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([OH:47])=[CH:43][C:42]=2[CH3:55])[N:36]=1)=[O:33]

Participants

6

Reactant 3

HCID 962WaterHCID 493570RiboflavinHCID 595478992,6-difluoro-N-[1-({2-methyl-4-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]benzamide

Product 1

HCID 595479572,6-Difluoro-N-{1-[(4-hydroxy-2-methylphenyl)methyl]-1H-pyrazol-3-yl}benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 10% palladium on carbon 50% wt water, degussa type E101 NE/W (406 mg, 3.82 mmol) was added under vacuum a solution of 2,6-difluoro-N-[1-({2-methyl-4-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]benzamide (for a preparation see Example 47)(1.79 g, 4.13 mmol) in ethyl acetate (30 ml). The suspension was hydrogenated at ambient temperature for 1.5 h. The suspension was filtered through a celite cartridge (10 g) and the cartridge washed with methanol (100 ml). The solvent was removed in vacuo to give the title compound as a grey foam (1.34 g);

Workup

  1. filtrationThe suspension was filtered through a celite cartridge (10 g)
  2. washthe cartridge washed with methanol (100 ml)
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5f325bb32a37432aa10b0c0d1ef3bfc4
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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