Hydrochloric Acid → 2-[(2-chloro-1-oxo-propyl)-amino]-beta-oxo-N-(2-pyridinyl)-3-trifluoromethyl-benzene-propanamide

HRID 1982596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1982596
[CH2:1]([Li])CCC.[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13](=[O:15])[CH3:14].[Cl:16][CH2:17][C:18]1[O:23][C:22](=[O:24])[C:21]2[CH:25]=[CH:26][CH:27]=[C:28]([C:29]([F:32])([F:31])[F:30])[C:20]=2[N:19]=1.Cl>CCCCCC.O1CCCC1.O>[Cl:16][CH:17]([CH3:1])[C:18]([NH:19][C:20]1[C:28]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](=[O:24])[CH2:14][C:13]([NH:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][N:6]=1)=[O:15])=[O:23]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 729292-AcetamidopyridineHCID 133813192-(1-chloromethyl)-8-trifluoromethyl-4H-3,1-benzoxazine-4-oneHCID 178418339Butyllithium

Produkt 1

HCID 134231002-[(2-chloro-1-oxo-propyl)-amino]-beta-oxo-N-(2-pyridinyl)-3-trifluoromethyl-benzene-propanamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

14 ml of a solution of butyllithium in hexane were added under argon at -5° to 0° C. over 30 minutes to a solution of 1.36 g of N-(2-pyridinyl)-acetamide in 27.2 ml of tetrahydrofuran and the mixture was stirred under argon at -5° C. for 15 minutes and was then cooled to -70° C. A solution of 1.38 g of 2-(1-chloromethyl)-8-trifluoromethyl-4H-3,1-benzoxazine-4-one [prepared in Step A of Example 14 of U.S. patent application Ser. No. 262,952] in 13.8 ml of tetrahydrofuran was added at -70° C. under argon over 30 minutes to the mixture which was stirred at -70° C. for one hour and was poured into a mixture of 200 ml of iced water and 10 ml of concentrated hydrochloric acid. The mixture was stirred at room temperature for 30 minutes and was extracted three times with 100 ml of ethyl acetate. The combined organic phases were washed twice with 75 ml of water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and eluted with an 8-2 ethyl acetate-cyclohexane mixture. The product was taken up in ether and the mixture was filtered. The product was dried to obtain 1.2 g of 2- [(2-chloro-1-oxo-propyl)-amino]-β-oxo-N-(2-pyridinyl)-3-trifluoromethyl-benzene-propanamide melting towards 150° C.

Aufarbeitung

  1. temperaturewas then cooled to -70° C
  2. stirringwas stirred at -70° C. for one hour
  3. stirringThe mixture was stirred at room temperature for 30 minutes
  4. extractionwas extracted three times with 100 ml of ethyl acetate
  5. washThe combined organic phases were washed twice with 75 ml of water
  6. customdried
  7. customevaporated to dryness under reduced pressure
  8. customThe residue was chromatographed over silica gel
  9. washeluted with an 8-2 ethyl acetate-cyclohexane mixture
  10. filtrationthe mixture was filtered
  11. customThe product was dried

Quellen und Nachweise

ORD-Eintrag
ord-c37bc1b28a33438daa17b86f46796890
Quelldatensatz
uspto-grants-1986_06
Patentnummer
US04596875

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