Water → Depyrazine 7,8-Dinitrophenyl Varenicline

HRID 2187560Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2187560
[N+:1]([C:4]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]2[CH:11]3[CH2:18][CH:7]([CH2:8][N:9](C(=O)C(F)(F)F)[CH2:10]3)[C:6]=2[CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[Na+].[Na+].O.CO.C(Cl)Cl>CO>[N+:15]([C:14]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]2[CH:7]3[CH2:18][CH:11]([CH2:10][NH:9][CH2:8]3)[C:12]=2[CH:13]=1)([O-:17])=[O:16]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 21226129Dichloromethane methanolHCID 218647441-(7,8-Dinitro-1,2,4,5-tetrahydro-3H-1,5-methano-3-benzazepin-3-yl)-2,2,2-trifluoroethan-1-one

Produkt 1

HCID 9878181Depyrazine 7,8-Dinitrophenyl Varenicline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1-(4,5-Dinitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-triflouroethanone (3.7 g, 10.7 mmol) and Na2CO3 (2.3 g, 21.4 mmol) were combined in MeOH (50 mL)) and H2O (20 mL) then warmed to reflux for 18 hours. The reaction was cooled, concentrated, treated with H2O and extracted with CH2Cl2 (3×50 mL) then dried through a cotton plug. After concentration. the residue was chromatographed to provide brown solids. (1.9 g. 71%). (TLC 5% MeOH/CH2Cl2 (NH3) Rf0.36). 1H NMR (400 MHz, CDCl3) δ7.69 (s, 2H), 3.17 (br s, 2H), 3.11 (d, J=12.6 Hz, 2H), 2.53 (m, 1H), 2.07 (d, J=11.0 Hz, 1H). GCMS m/e 249 (M+).

Aufarbeitung

  1. temperaturethen warmed
  2. temperatureto reflux for 18 hours
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. additiontreated with H2O
  6. extractionextracted with CH2Cl2 (3×50 mL)
  7. customthen dried through a cotton plug
  8. concentrationAfter concentration
  9. customthe residue was chromatographed
  10. customto provide brown solids

Quellen und Nachweise

ORD-Eintrag
ord-c8abf7582ecb4b2ab0b8467e63cc20e6
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06410550B1

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