2,2-Difluoroacetohydrazide → 7-bromo-1-(difluoromethyl)-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazine

HRID 1509301Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1509301
[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[NH:10][C:9](=S)[CH2:8][O:7][C:6]=2[N:12]=1.[F:19][CH:20]([F:25])[C:21]([NH:23][NH2:24])=O>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[N:10]3[C:21]([CH:20]([F:25])[F:19])=[N:23][N:24]=[C:9]3[CH2:8][O:7][C:6]=2[N:12]=1

Komponenten

4

Edukt 2

HCID 190657972,2-DifluoroacetohydrazideHCID 866836666-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazine-2(3H)-thione

Produkt 1

HCID 866836677-bromo-1-(difluoromethyl)-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazineAusbeute 22,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A mixture of 6-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazine-2(3H)-thione (0.21 g, 0.654 mmol) and 2,2-difluoroacetohydrazide (0.14 g, 1.3 mmol) in xylene (6 ml) was heated at 150 degree under microwave for 60 min. The reaction solution was concentrated and the residue was partitioned between ethyl acetate (10 ml) and water (10 ml). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (10 ml). The combined organic phase was concentrated and purified by column (biotage 25 g) eluted with ethyl acetate/cyclohexane (0-60%) to afford product (55 mg). 1H NMR (500 MHz, CDCl3) 8.09 (s, 1H), 7.4-7.55 (m, 5H), 7.06 (t, 1H), 5.66 (s, 2H).

Aufarbeitung

  1. temperaturewas heated at 150 degree under microwave for 60 min
  2. concentrationThe reaction solution was concentrated
  3. customthe residue was partitioned between ethyl acetate (10 ml) and water (10 ml)
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted with ethyl acetate (10 ml)
  6. concentrationThe combined organic phase was concentrated
  7. custompurified by column (biotage 25 g)
  8. washeluted with ethyl acetate/cyclohexane (0-60%)

Quellen und Nachweise

ORD-Eintrag
ord-75fa7c5eccc24c41b28851281d2c880a
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221838B2

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