Hydrochloric Acid → HCID 58255109, compound

HRID 536398Notes

Reaction equation

[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C@H:9]2[CH2:13][O:12][C:11](=[O:14])[NH:10]2)=[C:4]([CH3:15])[CH:3]=1.Cl[C:17]1[N:22]=[C:21]([NH:23][C:24]2[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=2)[C:20]([Cl:30])=[CH:19][N:18]=1.Cl>CC(O)C>[Cl:30][C:20]1[C:21]([NH:23][C:24]2[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=2)=[N:22][C:17]([NH:1][C:2]2[C:7]([CH3:8])=[CH:6][C:5]([C@H:9]3[CH2:13][O:12][C:11](=[O:14])[NH:10]3)=[C:4]([CH3:15])[CH:3]=2)=[N:18][CH:19]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a reaction tube was added (S)-4-(4-amino-2,5-dimethylphenyl)oxazolidin-2-one (48 mg, 0.23 mmol), 2,5-dichloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine (77 mg, 0.32 mmol), iPrOH (2 mL) and HCl (0.13 mL, 0.52 mmol, 4N in dioxane). The tube was then sealed and heated at 130° C. for 6 h. After cooling down to room temperature, the mixture was concentrated and purified by preparative RP-HPLC to provide (S)-4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethyl-phenyl)oxazolidin-2-one; ESMS m/z 414.1 (M+H+).

Workup

customThe tube was then sealed
temperatureAfter cooling down to room temperature
concentrationthe mixture was concentrated
custompurified by preparative RP-HPLC

Sources & evidence

ORD record: ord-94dc7f884f364549826bedd855b65a30
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859574B2

Reaction notes

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