N-[3-[2-[6-(Methylamino)-9H-purine-9-yl]ethenyl]-4-methylphenyl]-3-(trifluoromethyl)benzamide → N-(4-Methyl-3-(2-(6-(methylamino)-9H-purin-9-yl)ethyl)phenyl)-3-(trifluoromethyl)-benzamide

HRID 655793Notes

Reaction equation

HRID 655793 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[CH:4][C:3]=1/[CH:21]=[CH:22]/[N:23]1[CH:31]=[N:30][C:29]2[C:24]1=[N:25][CH:26]=[N:27][C:28]=2[NH:32][CH3:33]>CO.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[CH:11]=2)=[CH:4][C:3]=1[CH2:21][CH2:22][N:23]1[CH:31]=[N:30][C:29]2[C:24]1=[N:25][CH:26]=[N:27][C:28]=2[NH:32][CH3:33]

Participants

4

Reactant 1

HCID 15950818N-[3-[2-[6-(Methylamino)-9H-purine-9-yl]ethenyl]-4-methylphenyl]-3-(trifluoromethyl)benzamide

Product 1

HCID 23649898N-(4-Methyl-3-(2-(6-(methylamino)-9H-purin-9-yl)ethyl)phenyl)-3-(trifluoromethyl)-benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (E)-N-(4-methyl-3-(2-(6-(methylamino)-9H-purin-9-yl)vinyl)phenyl)-3-(trifluoromethyl)benzamide (0.10 g) in MeOH was added a catalytic amount of 10% palladium on carbon. The resulting mixture was hydrogenated under 50 psi H2 for 48 h at which point HPLC indicated completion. The catalyst was removed by filtration and the filtrate was concentrated on a rotavap and further dried under vacuum yielding the desired product.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated on a rotavap
  3. customfurther dried under vacuum

Sources & evidence

ORD record
ord-bb7c3e247da049cc9bf23584e6bebbda
Source dataset
uspto-grants-2011_12
Patent number
US08071609B2

Reaction notes

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