5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene → Chantix

HRID 914733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 914733
[CH:1]12[CH2:16][CH:12]([CH2:13][NH:14][CH2:15]1)[C:11]1[CH:10]=[C:9]3[C:4]([N:5]=[CH:6][CH:7]=[N:8]3)=[CH:3][C:2]2=1.[C:17]([OH:26])(=[O:25])[C@@H:18]([C@H:20]([C:22]([OH:24])=[O:23])[OH:21])[OH:19]>CO>[C:22]([C@@H:20]([C@H:18]([C:17]([OH:26])=[O:25])[OH:19])[OH:21])([OH:24])=[O:23].[CH:12]12[CH2:16][CH:1]([CH2:15][NH:14][CH2:13]1)[C:2]1[CH:3]=[C:4]3[C:9]([N:8]=[CH:7][CH:6]=[N:5]3)=[CH:10][C:11]2=1

Komponenten

4

Edukt 2

HCID 1703615,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaeneHCID 444305L-Tartaric acid2×

Produkt 1

HCID 9906942ChantixAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel3×

Reaktionsbedingungen

Temperatur
22.5 °C

Versuchsvorschrift

A reactor was charged with 5,8,14-triazatetracyclo[10.3.1.02,11.04,9]-hexadeca-2(11),3,5,7,9-pentaene free base (2 g; 0.0095 mole, 1.0 equiv.) and methanol (60 mL, 30 mL/g). The mixture was stirred at 20 to 25° C. until completely dissolved. A second reactor containing a solution of L-tartaric acid (1.55 g, 0.0103 mole, 1.1 equiv.) dissolved in methanol (60 mL, 30 mL/g) was heated to reflux in methanol (i.e., 60 to 66° C.). The free base solution was added to the L-tartaric acid solution at methanolic reflux temperature over 20 minutes. The resulting slurry was cooled to 20 to 25° C. over a 1 hour period. The reaction mixture was allowed to stir for approximately 2 hours followed by isolation of the product by filtration. The solid product was washed with methanol (10 mL), then dried under vacuum at 30 to 35° C. to give 3.3 grams (97%) of 5,8,14-triazatetracyclo[10.3.1.02,11.04,9]-hexadeca-2(11),3,5,7,9-pentaene L-tartrate Form A. The identity as Form A was determined by PXRD as compared with standard samples.

Aufarbeitung

  1. dissolutionuntil completely dissolved
  2. temperaturewas heated
  3. temperatureThe resulting slurry was cooled to 20 to 25° C. over a 1 hour period
  4. stirringto stir for approximately 2 hours
  5. filtrationfollowed by isolation of the product by filtration
  6. washThe solid product was washed with methanol (10 mL)
  7. customdried under vacuum at 30 to 35° C.

Quellen und Nachweise

ORD-Eintrag
ord-15220f13f81d483a888806b133df2085
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265119B2

Notizen zur Reaktion

Wird geladen…