7-羟基-6-甲氧基-3-((特戊酰氧基)甲基)-3,4-二氢喹唑啉-4-酮合成路线 （共 9 条）
反应条件
hydrogen; acetic acid; palladium on activated charcoal in methanol; ethyl acetate; N,N-dimethyl-formamide Hydrogenolysis; P=760 Torr; 0.666667 h;
参考文献
Zeneca Limited
Patent: US6265411 B1, 2001 ;
反应条件
1.1: NaH / dimethylformamide / 1.5 h 1.2: 84 percent / dimethylformamide / 2 h / 20 °C 2.1: 80 percent / H2; AcOH / 10 percent Pd/C / dimethylformamide; ethyl acetate; methanol / 0.67 h / 760 Torr View Scheme
参考文献
Hennequin, Laurent F.; Thomas, Andrew P.; Johnstone, Craig; Stokes, Elaine S. E.; Ple, Patrick A.; Lohmann, Jean-Jacques M.; Ogilvie, Donald J.; Dukes, Mike; Wedge, Steve R.; Curwen, Jon O.; Kendrew, Jane; Lambert-Van Der Brempt, Christine
Journal of Medicinal Chemistry, 1999 , vol. 42, # 26 p. 5369 - 5389
反应条件
1.1: dioxane / 24 h / Heating 1.2: 84 percent / NaOAc; AcOH / 3 h / Heating 2.1: NaH / dimethylformamide / 1.5 h 2.2: 84 percent / dimethylformamide / 2 h / 20 °C 3.1: 80 percent / H2; AcOH / 10 percent Pd/C / dimethylformamide; ethyl acetate; methanol / 0.67 h / 760 Torr View Scheme
参考文献
Hennequin, Laurent F.; Thomas, Andrew P.; Johnstone, Craig; Stokes, Elaine S. E.; Ple, Patrick A.; Lohmann, Jean-Jacques M.; Ogilvie, Donald J.; Dukes, Mike; Wedge, Steve R.; Curwen, Jon O.; Kendrew, Jane; Lambert-Van Der Brempt, Christine
Journal of Medicinal Chemistry, 1999 , vol. 42, # 26 p. 5369 - 5389
反应条件
1.1: NaH / dimethylformamide / 1.5 h 1.2: 84 percent / dimethylformamide / 2 h / 20 °C 2.1: 80 percent / H2; AcOH / 10 percent Pd/C / dimethylformamide; ethyl acetate; methanol / 0.67 h / 760 Torr View Scheme
参考文献
Hennequin, Laurent F.; Thomas, Andrew P.; Johnstone, Craig; Stokes, Elaine S. E.; Ple, Patrick A.; Lohmann, Jean-Jacques M.; Ogilvie, Donald J.; Dukes, Mike; Wedge, Steve R.; Curwen, Jon O.; Kendrew, Jane; Lambert-Van Der Brempt, Christine
Journal of Medicinal Chemistry, 1999 , vol. 42, # 26 p. 5369 - 5389
反应条件
1: 92 percent / Ph3P; DEAD / CH2Cl2 / 0.5 h / 20 °C 2: 92 percent / TFA / CH2Cl2 / 1 h / 20 °C 3: 82 percent / NaCNBH3 / tetrahydrofuran; methanol / 0.5 h / 20 °C 4: 83 percent / methanolic NH3 / methanol / 20 h / 20 °C 5: 98 percent / SOCl2 / dimethylformamide / 1 h / 85 °C View Scheme
参考文献
Hennequin, Laurent F.; Stokes, Elaine S. E.; Thomas, Andrew P.; Johnstone, Craig; Ple, Patrick A.; Ogilvie, Donald J.; Dukes, Michael; Wedge, Stephen R.; Kendrew, Jane; Curwen, Jon O.
Journal of Medicinal Chemistry, 2002 , vol. 45, # 6 p. 1300 - 1312
反应条件
triphenylphosphine; diethylazodicarboxylate in dichloromethane T=20°C; 0.5 h;
参考文献
AstraZeneca AB
Patent: EP1244647 B1, 2006 ;
Location in patent: Page/Page column 22-23 ;
EP 1244647 B1
反应条件
1: 7-hydroxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one With potassium carbonate in DMF (N,N-dimethyl-formamide) T=20°C; 0.5 h; 2: 1-(tert-butoxycarbonyl)-4-(4-methylphenylsulphonyloxymethyl)piperidine in DMF (N,N-dimethyl-formamide) T=100°C; 2 h;
参考文献
AstraZeneca AB
Patent: EP1119567 B1, 2005 ;
Location in patent: Page/Page column 45 ;
反应条件
1: 92 percent / Ph3P; DEAD / CH2Cl2 / 0.5 h / 20 °C
2: 92 percent / TFA / CH2Cl2 / 1 h / 20 °C
3: 82 percent / NaCNBH3 / tetrahydrofuran; methanol / 0.5 h / 20 °C
4: 83 percent / methanolic NH3 / methanol / 20 h / 20 °C
View Scheme
参考文献
Hennequin, Laurent F.; Stokes, Elaine S. E.; Thomas, Andrew P.; Johnstone, Craig; Ple, Patrick A.; Ogilvie, Donald J.; Dukes, Michael; Wedge, Stephen R.; Kendrew, Jane; Curwen, Jon O.
Journal of Medicinal Chemistry, 2002 , vol. 45, # 6 p. 1300 - 1312
反应条件
1: 100 percent / K2CO3 / dimethylformamide / 1.5 h / 90 °C
2: 100 percent / NH3 / methanol / 16 h
3: 80 percent / SOCl2; DMF / 2 h / Heating
View Scheme
参考文献
Ple, Patrick A.; Green, Tim P.; Hennequin, Laurent F.; Curwen, Jon; Fennell, Michael; Allen, Jack; Lambert-Van Der Brempt, Christine; Costello, Gerard
Journal of Medicinal Chemistry, 2004 , vol. 47, # 4 p. 871 - 887
