HCID 118209004, compound → HCID 117824590, compound

HRID 595270Notes

Reaction equation

HRID 595270 reaction equation
C([O:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][N:16]2[CH:20]=[C:19]([C:21]3[CH:22]=[C:23]([NH:28][C:29]4[N:34]=[C:33]([CH:35]([F:37])[F:36])[CH:32]=[CH:31][N:30]=4)[CH:24]=[C:25]([CH3:27])[CH:26]=3)[CH:18]=[N:17]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[F:37][CH:35]([F:36])[C:33]1[CH:32]=[CH:31][N:30]=[C:29]([NH:28][C:23]2[CH:22]=[C:21]([C:19]3[CH:18]=[N:17][N:16]([CH2:15][C:12]4[CH:11]=[CH:10][C:9](=[O:8])[NH:14][CH:13]=4)[CH:20]=3)[CH:26]=[C:25]([CH3:27])[CH:24]=2)[N:34]=1

Participants

4

Reactant 1

HCID 118209004HCID 118209004, compound

Product 1

HCID 117824590HCID 117824590, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of N-[3-(1-{[6-(benzyloxy)pyridin-3-yl]methyl}-1H-pyrazol-4-yl)-5-methylphenyl]-4-(difluoromethyl)pyrimidin-2-amine (80 mg, 0.16 mmol) in methanol (20 mL) was added palladium hydroxide on carbon (20 wt %, 8 mg). The reaction mixture was stirred at 25° C. under a hydrogen atmosphere (1 atm) for 12 hours. The mixture was then filtered and concentrated under reduced pressure. The residue was purified by reverse phase HPLC to give the 5-{[4-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]methyl}pyridin-2(1H)-one. MS ESI calc'd. for C21H19F2N6O [M+H]+ 409. found 409.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-acb394bae180402a8689b1d70cff4457
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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