Water → (4-Hydroxy-3-trifluoromethyl-phenyl)-(7-methyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone

HRID 1943739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943739
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].S(Cl)(Cl)=O.C[N:20]1[CH:25]2[O:26][CH2:27][CH2:28][NH:29][C:24]2=[CH:23][CH:22]=[CH:21]1.O.[CH3:31]N(C)C(=O)C>>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:29]2[CH2:28][CH2:27][O:26][C:25]3[N:20]=[CH:21][C:22]([CH3:31])=[CH:23][C:24]2=3)=[O:8])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]

Komponenten

6

Edukt 5

HCID 962WaterHCID 24386Thionyl ChlorideHCID 31374Dimethylacetamide2×HCID 27751124-Hydroxy-3-(trifluoromethyl)benzoic acidHCID 669365305-methyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine

Produkt 1

HCID 44608711(4-Hydroxy-3-trifluoromethyl-phenyl)-(7-methyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

4-hydroxy-3-trifluoromethyl-benzoic acid (151 mg, 0.73 mmol) was dissolved in N,N-dimethyl acetamide (2.0 ml) and then cooled to −20° C. Thionyl chloride (0.073 ml, 100 mmol) was added thereto and stirred at −20° C. for 30 minutes. 5-methyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine dissolved in N,N-dimethyl acetamide (1.0 ml) was added thereto dropwise and then stirred at −20° C. for 20 minutes, and then stirred at room temperature for 15 hours. Water was added thereto and the mixture was extracted with dichloromethane, and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The resulting solid residue was recrystallized from dichloromethane to obtain the target compound 69, i.e., (4-hydroxy-3-trifluoromethyl-phenyl)-(7-methyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone, as white solid (176 mg, 78%).

Aufarbeitung

  1. additionwas added
  2. stirringdropwise and then stirred at −20° C. for 20 minutes
  3. stirringstirred at room temperature for 15 hours
  4. extractionthe mixture was extracted with dichloromethane
  5. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe resulting solid residue was recrystallized from dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-c3cbd4800d9746ce9e0ad489328da1e1
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394792B2

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