5-(imino-morpholin-4-yl-methyl)-3,4-dihydro-1H-isoquinoline → 2-[5-(imino-morpholin-4-yl-methyl)-3,4-dihydro-1H-isoquinolin-2-yl]-6,7-dimethoxy-3H-quinazolin-4-one

HRID 8733

Reaktionsgleichung

Cl[C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[NH:17]=[C:18]([N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)[C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][NH:23][CH2:24]2>COC(O)C>[NH:17]=[C:18]([N:29]1[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1)[C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][N:23]([C:2]1[NH:11][C:10](=[O:12])[C:9]3[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=3)[N:3]=1)[CH2:24]2

Komponenten

Reaktionsbedingungen

Temperatur: 95 °C

Versuchsvorschrift

A mixture of 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 1b(0.159 g, 0.62 mmol) and 5-(imino-morpholin-4-yl-methyl)-3,4-dihydro-1H-isoquinoline 28a (0.179 g, 0.69 mmol) in methoxyethanol (10 mL) was heated to 95° C. with stirring for 18 h. the volatiles were evaporated and the residue was purified by flash column eluting with 2% methanol in dichloromethane containing 0.2% of ammonium hydroxide to yield 50 mg of 2-[5-(imino-morpholin-4-yl-methyl)-3,4-dihydro-1H-isoquinolin-2-yl]-6,7-dimethoxy-3H-quinazolin-4-one 901. The product was converted to the hydrochloric acid salt, mp. 249–251° C., [M+H]+=450.

Aufarbeitung

customwere evaporated
customthe residue was purified by flash column
washeluting with 2% methanol in dichloromethane containing 0.2% of ammonium hydroxide

Quellen und Nachweise

ORD-Eintrag: ord-75d4b318f11f4445b2f0c64e9eaf1b7a
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07091200B2

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