4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)-1-(4-methoxybenzyl)piperidin-2-one → 4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)piperidin-2-one

HRID 536373Notes

Reaction equation

HRID 536373 reaction equation
[Cl:1][C:2]1[C:3]([NH:33][C:34]2[CH:38]=[C:37]([CH3:39])[NH:36][N:35]=2)=[N:4][C:5]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH:16]3[CH2:21][CH2:20][N:19](CC4C=CC(OC)=CC=4)[C:18](=[O:31])[CH2:17]3)=[C:11]([CH3:32])[CH:10]=2)=[N:6][CH:7]=1>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[C:3]([NH:33][C:34]2[CH:38]=[C:37]([CH3:39])[NH:36][N:35]=2)=[N:4][C:5]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH:16]3[CH2:21][CH2:20][NH:19][C:18](=[O:31])[CH2:17]3)=[C:11]([CH3:32])[CH:10]=2)=[N:6][CH:7]=1

Participants

3

Reactant 1

HCID 671555134-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)-1-(4-methoxybenzyl)piperidin-2-one

Product 1

HCID 582549614-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)piperidin-2-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)-1-(4-methoxybenzyl)piperidin-2-one (45 mg) in TFA (0.5 mL) was heated to 100° C. for 24 hr. After cooling down to room temperature, the mixture was concentrated and purified by preparative RP-HPLC to provide 4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)piperidin-2-one. ESMS m/z 426.2 (M+H+).

Workup

  1. concentrationthe mixture was concentrated
  2. custompurified by preparative RP-HPLC

Sources & evidence

ORD record
ord-d1e18d411f964169918298605c646478
Source dataset
uspto-grants-2014_10
Patent number
US08859574B2

Reaction notes

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