Reaktionsgleichung
C(OC(=O)[NH:7]CCCCNC1C2C(=CC(Br)=CC=2)N=CC=1N)(C)(C)C.C(Cl)(=O)CCC.[C:32]([O:36][C:37](=[O:60])[NH:38][CH2:39][CH2:40][CH2:41][CH2:42][N:43]1[C:55]2[C:54]3[CH:53]=[CH:52][C:51]([Br:56])=[CH:50][C:49]=3[N:48]=[CH:47][C:46]=2[N:45]=[C:44]1[CH2:57][CH2:58][CH3:59])([CH3:35])([CH3:34])[CH3:33]>>[C:32]([O:36][C:37](=[O:60])[NH:38][CH2:39][CH2:40][CH2:41][CH2:42][N:43]1[C:55]2[C:54]3[CH:53]=[CH:52][C:51]([Br:56])=[CH:50][C:49]=3[N:48]=[C:47]([NH2:7])[C:46]=2[N:45]=[C:44]1[CH2:57][CH2:58][CH3:59])([CH3:35])([CH3:34])[CH3:33]Komponenten
Edukt 3
Produkt 1
Versuchsvorschrift
tert-Butyl[4-(3-amino-7-bromoquinolin-4-ylamino)butyl]carbamate was treated with butyryl chloride and cyclized according to the methods described in Part C and D of Examples 125–135. The resulting product, tert-butyl[4-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate was oxidized and aminated according to the methods described in Parts H and I of Example 1 to afford tert-butyl[4-(4-amino-7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate, which was coupled with 3-pyridylboronic acid according to the method described in Part J of Example 1. The reaction was heated at reflux for four hours, and the work-up procedure described in Part F of Examples 125–135 was followed. The crude product was recrystallized from toluene (1 mL/g) to provide tert-butyl {4-[4-amino-2-propyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}carbamate as a tan powder, mp 136–138° C.
Quellen und Nachweise
- ORD-Eintrag
- ord-5987f786235c405b8c7944aed4cb6087
- Quelldatensatz
- uspto-grants-2006_08
- Patentnummer
- US07091214B2
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