(+)-4-[(ΑR)-Α-((2S,5R)-4-烯丙基-2,5-二甲基-1-哌嗪基)-3-甲氧基苄基]-N,N-二乙基苯酰胺合成路线 (共 11 条)
反应条件
1: N,N-diethylbenzamide-4-carboxaldehyde; (-)-(2R,5S)-1-allyl-2,5-dimethylpiperazine With 1,2,3-Benzotriazole in toluene
2 - 3 h; Heating / reflux;
2: (3-methoxyphenyl)-magnesium bromide T=0 - 20°C; 1.5 h;
3: With water; ammonium chloride
参考文献
MOUNT COOK BIOSCIENCES, INC.
Patent: WO2007/27987 A2, 2007 ;
Location in patent: Page/Page column 23-24 ;
WO 2007/027987 A2
反应条件
potassium carbonate in acetonitrile
72 h; Heating;
参考文献
Calderon, Silvia N.; Rice, Kenner C.; Rothman, Richard B.; Porreca, Frank; Flippen-Anderson, Judith L.; Kayakiri, Hiroshi; Xu, Heng; Becketts, Karen; Smith, Larren E.; Bilsky, Edward J.; Davis, Peg; Horvath, Robert
Journal of Medicinal Chemistry, 1997 , vol. 40, # 5 p. 695 - 704
反应条件
1: 53 percent / KMnO4 / 2-methyl-propan-2-ol; H2O / 7.5 h / Heating
2: SOCl2 / benzene / 3 h / Heating
3: CHCl3 / 4 h / Ambient temperature
4: 70 percent / NaBH4 / ethanol; H2O / 2 h / Heating
5: 11.16 g / 37percent aq. HCl / CHCl3 / Ambient temperature
6: 29 percent / K2CO3 / acetonitrile / 72 h / Heating
View Scheme
参考文献
Calderon, Silvia N.; Rice, Kenner C.; Rothman, Richard B.; Porreca, Frank; Flippen-Anderson, Judith L.; Kayakiri, Hiroshi; Xu, Heng; Becketts, Karen; Smith, Larren E.; Bilsky, Edward J.; Davis, Peg; Horvath, Robert
Journal of Medicinal Chemistry, 1997 , vol. 40, # 5 p. 695 - 704
反应条件
1: CHCl3 / 4 h / Ambient temperature
2: 70 percent / NaBH4 / ethanol; H2O / 2 h / Heating
3: 11.16 g / 37percent aq. HCl / CHCl3 / Ambient temperature
4: 29 percent / K2CO3 / acetonitrile / 72 h / Heating
View Scheme
参考文献
Calderon, Silvia N.; Rice, Kenner C.; Rothman, Richard B.; Porreca, Frank; Flippen-Anderson, Judith L.; Kayakiri, Hiroshi; Xu, Heng; Becketts, Karen; Smith, Larren E.; Bilsky, Edward J.; Davis, Peg; Horvath, Robert
Journal of Medicinal Chemistry, 1997 , vol. 40, # 5 p. 695 - 704
反应条件
1: SOCl2 / benzene / 3 h / Heating
2: CHCl3 / 4 h / Ambient temperature
3: 70 percent / NaBH4 / ethanol; H2O / 2 h / Heating
4: 11.16 g / 37percent aq. HCl / CHCl3 / Ambient temperature
5: 29 percent / K2CO3 / acetonitrile / 72 h / Heating
View Scheme
参考文献
Calderon, Silvia N.; Rice, Kenner C.; Rothman, Richard B.; Porreca, Frank; Flippen-Anderson, Judith L.; Kayakiri, Hiroshi; Xu, Heng; Becketts, Karen; Smith, Larren E.; Bilsky, Edward J.; Davis, Peg; Horvath, Robert
Journal of Medicinal Chemistry, 1997 , vol. 40, # 5 p. 695 - 704
反应条件
1: 39.65 g / ethanol / Ambient temperature
3: 29 percent / K2CO3 / acetonitrile / 72 h / Heating
View Scheme
参考文献
Calderon, Silvia N.; Rice, Kenner C.; Rothman, Richard B.; Porreca, Frank; Flippen-Anderson, Judith L.; Kayakiri, Hiroshi; Xu, Heng; Becketts, Karen; Smith, Larren E.; Bilsky, Edward J.; Davis, Peg; Horvath, Robert
Journal of Medicinal Chemistry, 1997 , vol. 40, # 5 p. 695 - 704
反应条件
1: EDCI / CH2Cl2
2: benzene / Heating
3: tetrahydrofuran / 3 h / 20 °C
View Scheme
参考文献
Furness; Zhang; Coop; Jacobson; Rothman; Dersch; Xu; Porreca; Rice
Journal of Medicinal Chemistry, 2000 , vol. 43, # 16 p. 3193 - 3196
反应条件
1: 84 percent / AlCl3 / nitromethane / 0.75 h / Ambient temperature
2: 53 percent / KMnO4 / 2-methyl-propan-2-ol; H2O / 7.5 h / Heating
3: SOCl2 / benzene / 3 h / Heating
4: CHCl3 / 4 h / Ambient temperature
5: 70 percent / NaBH4 / ethanol; H2O / 2 h / Heating
6: 11.16 g / 37percent aq. HCl / CHCl3 / Ambient temperature
7: 29 percent / K2CO3 / acetonitrile / 72 h / Heating
View Scheme
参考文献
Calderon, Silvia N.; Rice, Kenner C.; Rothman, Richard B.; Porreca, Frank; Flippen-Anderson, Judith L.; Kayakiri, Hiroshi; Xu, Heng; Becketts, Karen; Smith, Larren E.; Bilsky, Edward J.; Davis, Peg; Horvath, Robert
Journal of Medicinal Chemistry, 1997 , vol. 40, # 5 p. 695 - 704
反应条件
1: 84 percent / AlCl3 / nitromethane / 0.75 h / Ambient temperature
2: 53 percent / KMnO4 / 2-methyl-propan-2-ol; H2O / 7.5 h / Heating
3: SOCl2 / benzene / 3 h / Heating
4: CHCl3 / 4 h / Ambient temperature
5: 70 percent / NaBH4 / ethanol; H2O / 2 h / Heating
6: 11.16 g / 37percent aq. HCl / CHCl3 / Ambient temperature
7: 29 percent / K2CO3 / acetonitrile / 72 h / Heating
View Scheme
参考文献
Calderon, Silvia N.; Rice, Kenner C.; Rothman, Richard B.; Porreca, Frank; Flippen-Anderson, Judith L.; Kayakiri, Hiroshi; Xu, Heng; Becketts, Karen; Smith, Larren E.; Bilsky, Edward J.; Davis, Peg; Horvath, Robert
Journal of Medicinal Chemistry, 1997 , vol. 40, # 5 p. 695 - 704
反应条件
in tetrahydrofuran
T=20°C; Substitution; 3 h;
参考文献
Furness; Zhang; Coop; Jacobson; Rothman; Dersch; Xu; Porreca; Rice
Journal of Medicinal Chemistry, 2000 , vol. 43, # 16 p. 3193 - 3196