(S)-N-(2-chloroethyl)-5-(4-(5-fluoro-2-methoxypyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide → (S)-N-(2-chloroethyl)-5-(4-(5-fluoro-2-oxo-1,2-dihydropyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 1426966Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:8]=[N:9][N:10]2[CH:15]=[CH:14][C:13]([N:16]3[C@@H:20]([C:21]4[C:22]([O:28]C)=[N:23][CH:24]=[C:25]([F:27])[CH:26]=4)[CH2:19][O:18][C:17]3=[O:30])=[N:12][C:11]=12)=[O:6]>Cl.CC(O)C>[Cl:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:8]=[N:9][N:10]2[CH:15]=[CH:14][C:13]([N:16]3[C@@H:20]([C:21]4[C:22](=[O:28])[NH:23][CH:24]=[C:25]([F:27])[CH:26]=4)[CH2:19][O:18][C:17]3=[O:30])=[N:12][C:11]=12)=[O:6]

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of (S)-N-(2-chloroethyl)-5-(4-(5-fluoro-2-methoxypyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (80 mg, 0.18 mmol) in 5-6N HCl/IPA (2.5 mL) was warmed to 90° C. in a sealed tube for 1.5 hours. The cooled mixture was filtered and the filtrate was concentrated. The residue was concentrated twice from Et2O and dried under reduced pressure to afford (S)-N-(2-chloroethyl)-5-(4-(5-fluoro-2-oxo-1,2-dihydropyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (63 mg, 82% yield) as a beige solid. MS (apci) m/z=421.0 (M+H).

Workup

filtrationThe cooled mixture was filtered
concentrationthe filtrate was concentrated
concentrationThe residue was concentrated twice from Et2O
customdried under reduced pressure

Sources & evidence

ORD record: ord-f2a0517631064707b5715f542d5a349c
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933084B2

Reaction notes

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