Hydroxyamine hydrochloride → 4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)-cyclohexanone oxime

HRID 2093806Notes

Reaction equation

HRID 2093806 reaction equation
[Cl:1][C:2]1[C:3]([NH:24][C:25]2[CH:29]=[C:28]([CH3:30])[NH:27][N:26]=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][C:19](=O)[CH2:18][CH2:17]3)=[C:11]([CH3:23])[CH:10]=2)=[N:6][CH:7]=1.CC([O-])=O.[Na+].[NH2:36][OH:37].Cl>CO>[Cl:1][C:2]1[C:3]([NH:24][C:25]2[CH:29]=[C:28]([CH3:30])[NH:27][N:26]=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][C:19](=[N:36][OH:37])[CH2:18][CH2:17]3)=[C:11]([CH3:23])[CH:10]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 671668434-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)cyclohexanone

Product 1

HCID 446215804-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)-cyclohexanone oxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)cyclohexanone (15 mg, 0.033 mmol) in MeOH (0.5 mL) was added NaOAc (6 mg, 0.073 mmol) and NH2OH HCl (5 mg, 0.073 mmol). The resulting mixture was stirred at 70° C. for 2 h. and then cooled down to room temperature. The mixture was purified directly by preparative RP-HPLC to provide 4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)-cyclohexanone oxime; ESMS m/z 440.2 (M+H+).

Workup

  1. temperaturecooled down to room temperature
  2. customThe mixture was purified directly by preparative RP-HPLC

Sources & evidence

ORD record
ord-5940c65961e349e0b057941729dbb108
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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