Cyanogen Bromide → (S)-3-(3-(4-(5-amino-1,3,4-oxadiazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(4-fluorophenyl)oxazolidin-2-one

HRID 539125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539125
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][O:11][C:10](=[O:13])[N:9]2[C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]4[CH:32]=[CH:31][C:26]([C:27]([NH:29][NH2:30])=[O:28])=[CH:25][CH:24]=4)=[C:16]3[N:15]=2)=[CH:4][CH:3]=1.[N:33]#[C:34]Br.C([O-])(O)=O.[Na+]>O1CCOCC1.O.CCOC(C)=O>[NH2:33][C:34]1[O:28][C:27]([C:26]2[CH:31]=[CH:32][C:23]([C:22]3[CH:21]=[N:20][N:17]4[CH:18]=[CH:19][C:14]([N:9]5[C@@H:8]([C:5]6[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=6)[CH2:12][O:11][C:10]5=[O:13])=[N:15][C:16]=34)=[CH:24][CH:25]=2)=[N:29][N:30]=1

Komponenten

7

Edukt 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 67035490(S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide

Produkt 1

HCID 67034511(S)-3-(3-(4-(5-amino-1,3,4-oxadiazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(4-fluorophenyl)oxazolidin-2-oneAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a suspension of (S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide (0.040 g, 0.0925 mmol) in dioxane (4 mL) was added cyanic bromide (0.0216 g, 0.204 mmol) followed by a solution of NaHCO3 (0.00933 g, 0.111 mmol) in water (0.9 mL). The resulting mixture was stirred at ambient temperature overnight, then diluted with EtOAc. The organic layer was washed with brine and water, dried (phase separator silicone treated filter paper) and concentrated. The crude material was purified on silica gel (2-5% MeOH in DCM) to provide (S)-3-(3-(4-(5-amino-1,3,4-oxadiazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(4-fluorophenyl)oxazolidin-2-one (0.0066 g, 16% yield). LCMS (APCI+) m/z 458 [M+H]+.

Aufarbeitung

  1. washThe organic layer was washed with brine and water
  2. customdried
  3. addition(phase separator silicone treated filter paper)
  4. concentrationconcentrated
  5. customThe crude material was purified on silica gel (2-5% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-229b5807c8ed4616a99e4fc427e2c048
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865726B2

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