Acetonitrile → Methyl 2-(3-((5-methylisoxazol-3-yl)oxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinate

HRID 72448

Reaktionsgleichung

Reaktionsgleichung von HRID 72448
[CH3:1][C:2]1[O:6][N:5]=[C:4]([OH:7])[CH:3]=1.C(#N)C.CS(O[CH:16]1[CH2:19][N:18]([C:20]2[N:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:21]=2[C:22]([O:24][CH3:25])=[O:23])[CH2:17]1)(=O)=O>>[CH3:1][C:2]1[O:6][N:5]=[C:4]([O:7][CH:16]2[CH2:19][N:18]([C:20]3[N:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][C:21]=3[C:22]([O:24][CH3:25])=[O:23])[CH2:17]2)[CH:3]=1

Komponenten

4

Edukt 3

HCID 6342AcetonitrileHCID 24781HymexazolHCID 86697871Methyl 2-(3-((methylsulfonyl)oxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinate

Produkt 1

HCID 67958466Methyl 2-(3-((5-methylisoxazol-3-yl)oxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinateAusbeute 16,5 %

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

To a solution of 5-methylisoxazol-3-ol (33.48 mg, 0.34 mmol) in acetonitrile (0.7 ml) potassium carbonate (60.85 mg, 0.44 mmol) was added followed by addition of methyl 2-(3-((methylsulfonyl)oxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinate (D68) (120 mg, 0.34 mmol). The reaction mixture was heated at 180° C. under microwave irradiation for 25 min. After solvent evaporation the residue was purified by Biotage SNAP-Si column (10 g) eluting with cycloexane/ethyl acetate from 95/05 to 70/30. Collected fractions were evaporated in vacuo tot afford the title compound (D88) (20 mg)

Aufarbeitung

  1. customAfter solvent evaporation the residue
  2. customwas purified by Biotage SNAP-Si column (10 g)
  3. washeluting with cycloexane/ethyl acetate from 95/05 to 70/30
  4. customCollected fractions were evaporated in vacuo tot

Quellen und Nachweise

ORD-Eintrag
ord-b976eb125a6d42849a39235dbb30c1df
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828987B2

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