Acetic Acid → 1-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)ethanone O-2-hydroxyethyl oxime

HRID 2093804Notes

Reaction equation

[Cl:1][C:2]1[C:3]([NH:20][C:21]2[CH:25]=[C:24]([CH3:26])[NH:23][N:22]=2)=[N:4][C:5]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([C:16](=O)[CH3:17])=[C:11]([CH3:19])[CH:10]=2)=[N:6][CH:7]=1.CC(O)=O.[NH2:31][O:32][CH2:33][CH2:34][OH:35]>CO>[OH:35][CH2:34][CH2:33][O:32][N:31]=[C:16]([C:12]1[CH:13]=[C:14]([CH3:15])[C:9]([NH:8][C:5]2[N:4]=[C:3]([NH:20][C:21]3[CH:25]=[C:24]([CH3:26])[NH:23][N:22]=3)[C:2]([Cl:1])=[CH:7][N:6]=2)=[CH:10][C:11]=1[CH3:19])[CH3:17]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)ethanone (60 mg, 0.16 mmol) in MeOH (1 mL) was added AcOH (15 mg, 0.25 mmol), followed by the addition of 2-(aminooxy)ethanol (20 mg, 0.26 mmol). The mixture was heated to 60° C. for 14 h and cooled down to room temperature. The mixture was then purified directly by preparative RP-HPLC to provide 1-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)ethanone O-2-hydroxyethyl oxime; ESMS m/z 430.2 (M+H+).

Workup

temperaturecooled down to room temperature
customThe mixture was then purified directly by preparative RP-HPLC

Sources & evidence

ORD record: ord-eafe4017470a4b949f0853b505462415
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445505B2

Reaction notes

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