(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 1426966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426966
[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]

Komponenten

3

Edukt 1

HCID 86691748(S)-N-(2-chloroethyl)-5-(4-(5-fluoro-2-methoxypyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Produkt 1

HCID 86691749(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-carboxamideAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21912024Isopropanol hydrochlorideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

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).

Aufarbeitung

  1. filtrationThe cooled mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. concentrationThe residue was concentrated twice from Et2O
  4. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f2a0517631064707b5715f542d5a349c
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933084B2

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