HCID 178418361, compound → HCID 178449200, compound

HRID 2280417Notes

Reaction equation

HRID 2280417 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([NH:20]/[C:21](/[NH:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[N:22]\[C:23](=[O:34])[C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)[NH:17][N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:36]([NH:35]/[C:21](/[NH:20][C:18]1[NH:17][N:16]=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)[CH:19]=1)=[N:22]/[C:23](=[O:34])[C:24]1[CH:25]=[CH:26][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:28][CH:29]=1)([CH3:39])([CH3:37])[CH3:38]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178449201HCID 178449201, compound

Product 1

HCID 178449200HCID 178449200, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(Z)—N-(((3-(4-(Benzyloxy)phenyl)-1H-pyrazol-5-yl)amino)(tert-butylamino)methylene)-4-(trifluoromethyl)benzamide (150 mg) was dissolved in methanol (10 mL) and the solution was degassed with nitrogen. To the solution was added 10% palladium on carbon (30 mg, 0.1 equiv). The mixture was subjected to hydrogen gas at 60 psi pressure in a Parr shaker. The reaction was checked periodically for completion. Upon completion, the reaction mixture was filtered through celite, and the filtrate was concentrated in vacuo to provide the crude product, which was purified by silica chromatography (9:1 to 55:45 hexanes:EtOAc) to provide the title compound (85 mg, 68% yield).

Workup

  1. customthe solution was degassed with nitrogen
  2. filtrationUpon completion, the reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto provide the crude product, which
  5. customwas purified by silica chromatography (9:1 to 55:45 hexanes:EtOAc)

Sources & evidence

ORD record
ord-5caf9ebb8fec44fdb32078c7576e521f
Source dataset
uspto-grants-2015_09
Patent number
US09139532B2

Reaction notes

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