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

HRID 1426965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426965
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[CH2:14][O:13][C:12](=[O:15])[NH:11]2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[H-].[Na+].Cl[C:19]1[CH:24]=[CH:23][N:22]2[N:25]=[CH:26][C:27]([C:28]([NH:30][CH2:31][CH2:32][Cl:33])=[O:29])=[C:21]2[N:20]=1.[NH4+].[Cl-]>CN(C=O)C.O>[Cl:33][CH2:32][CH2:31][NH:30][C:28]([C:27]1[CH:26]=[N:25][N:22]2[CH:23]=[CH:24][C:19]([N:11]3[C@@H:10]([C:4]4[C:5]([O:8][CH3:9])=[N:6][CH:7]=[C:2]([F:1])[CH:3]=4)[CH2:14][O:13][C:12]3=[O:15])=[N:20][C:21]=12)=[O:29]

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86691741(S)-4-(5-fluoro-2-methoxypyridin-3-yl)oxazolidin-2-oneHCID 866917475-chloro-N-(2-chloroethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Produkt 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-carboxamideAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (S)-4-(5-fluoro-2-methoxypyridin-3-yl)oxazolidin-2-one (prepared according to Example 30; 50 mg, 0.236 mmol) in DMF (1 mL) was added sodium hydride (11 mg, 0.28 mmol, 60% in mineral oil). The mixture was stirred at ambient temperature for 20 minutes, then treated with 5-chloro-N-(2-chloroethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (61 mg, 0.236 mmol). The mixture was stirred at 16 hours, and then treated with saturated NH4Cl solution (10 mL) and water (20 mL). The resulting precipitate was collected by filtration, washed with water and Et2O, then dried under reduced pressure to afford (S)-N-(2-chloroethyl)-5-(4-(5-fluoro-2-methoxypyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (83 mg, 81% yield) as a beige solid. MS (apci) m/z=434.9 (M+H).

Aufarbeitung

  1. stirringThe mixture was stirred at 16 hours
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water and Et2O
  4. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-55f8413649d24305b0a69a0cc4fc660f
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933084B2

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