6-溴-N-甲基-2-萘甲酰胺合成路线 （共 9 条）
反应条件
1: 6-bromo-2-naphthalenecarboxylic acid With thionyl chloride; N,N-dimethyl-formamide in toluene T=45 - 50°C; 1 h; 2: methylamine With triethylamine in methanol; toluene T=10 - 25°C; 1 h;
参考文献
WO2012/173280 A1, ;
Page/Page column 32-33 ;
反应条件
1.1: 2-(trifluoromethyl)phenyllithium / tetrahydrofuran; hexane / 0.83 h / -65 - -55 °C / Inert atmosphere 1.2: 1.5 h / -65 °C / Inert atmosphere 1.3: Inert atmosphere 2.1: ethanol 3.1: sodium hydroxide / water View Scheme
参考文献
TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAWABATA, Yoichi; SAWAI, Yasuhiro; KANNO, Kazuaki; SAWADA, Naotaka
Patent: WO2012/173280 A1, 2012 ;
反应条件
1.1: 2-(trifluoromethyl)phenyllithium / tetrahydrofuran; hexane / 0.83 h / -65 - -55 °C / Inert atmosphere 1.2: 1.5 h / -65 °C / Inert atmosphere 1.3: Inert atmosphere 2.1: Chiralpak AD column / ethanol; hexane / Resolution of racemate; HPLC conditions View Scheme
参考文献
Ruchelman, Alexander L.; Man, Hon-Wah; Chen, Roger; Liu, Wei; Lu, Ling; Cedzik, Dorota; Zhang, Ling; Leisten, Jim; Collette, Alice; Narla, Rama Krishna; Raymon, Heather K.; Muller, George W.
Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 21 p. 6356 - 6374
反应条件
1.1: n-butyllithium; Di-n-butylmagnesium / hexane; tetrahydrofuran / 1.5 h / -11 - 20 °C / Inert atmosphere 1.2: 7.5 h / -11 °C 2.1: manganese(IV) oxide / isobutyramide / 60 h / 25 °C / Inert atmosphere View Scheme
参考文献
TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAWABATA, Yoichi; SAWAI, Yasuhiro; KANNO, Kazuaki; SAWADA, Naotaka
Patent: WO2012/173280 A1, 2012 ;
反应条件
1.1: 2-(trifluoromethyl)phenyllithium / tetrahydrofuran; hexane / 0.83 h / -65 - -55 °C / Inert atmosphere
1.2: 1.5 h / -65 °C / Inert atmosphere
1.3: Inert atmosphere
2.1: Chiralpak AD column / ethanol; hexane / Resolution of racemate; HPLC conditions
View Scheme
参考文献
Ruchelman, Alexander L.; Man, Hon-Wah; Chen, Roger; Liu, Wei; Lu, Ling; Cedzik, Dorota; Zhang, Ling; Leisten, Jim; Collette, Alice; Narla, Rama Krishna; Raymon, Heather K.; Muller, George W.
Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 21 p. 6356 - 6374
反应条件
1: 6-bromo-N-methyl-2-naphthamide With 2-(trifluoromethyl)phenyllithium in tetrahydrofuran; hexane
T=-65 - -55°C; 0.833333 h; Inert atmosphere;
2: 5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one in tetrahydrofuran; hexane
T=-65°C; 1.5 h; Inert atmosphere;
3: With water; ammonium chloride in tetrahydrofuran; hexane
Inert atmosphere;
参考文献
Ruchelman, Alexander L.; Man, Hon-Wah; Chen, Roger; Liu, Wei; Lu, Ling; Cedzik, Dorota; Zhang, Ling; Leisten, Jim; Collette, Alice; Narla, Rama Krishna; Raymon, Heather K.; Muller, George W.
Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 21 p. 6356 - 6374
反应条件
ammonia in tetrahydrofuran
参考文献
Tasaka, Akihiro; Hitaka, Takenori; Matsunaga, Nobuyuki; Kusaka, Masami; Adachi, Mari; Oaki, Isao; Ojida, Akio
Patent: US2004/33935 A1, 2004 ;
反应条件
ammonia in tetrahydrofuran
参考文献
Tasaka, Akihiro; Hitaka, Takenori; Matsunaga, Nobuyuki; Kusaka, Masami; Adachi, Mari; Oaki, Isao; Ojida, Akio
Patent: US2004/33935 A1, 2004 ;
反应条件
1.1: n-butyllithium; Di-n-butylmagnesium / hexane; tetrahydrofuran / 1.5 h / -11 - 20 °C / Inert atmosphere
1.2: 7.5 h / -11 °C
2.1: manganese(IV) oxide / isobutyramide / 60 h / 25 °C / Inert atmosphere
3.1: pyridine; cinchonine / tetrahydrofuran / 1.75 h / -25 °C / Inert atmosphere
4.1: calcium chloride; sodium tetrahydroborate / ethanol; tetrahydrofuran / 8.5 h / -7 - 5 °C
4.2: 5 °C
View Scheme
参考文献
TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAWABATA, Yoichi; SAWAI, Yasuhiro; KANNO, Kazuaki; SAWADA, Naotaka
Patent: WO2012/173280 A1, 2012 ;
