5-甲氧基-n-丙基-2-氨基四氢化萘盐酸盐合成路线 (共 10 条)
反应条件
1: potassium carbonate / 2-methyl tetrahydrofuran / Reflux 2: methyltretrahydrofuran, 2- / 75 °C 3: hydrogenchloride / water; tetrahydrofuran / 0.25 h / 65 °C View Scheme
参考文献
UCB PHARMA GMBH; ATES, Celal; SCHULE, Arnaud; PALACIO, Magali; DEUTSCH, Paul; VASSELIN, David; CARLY, Nicolas; PHADTARE, Ganesh; YERANDE, Swapnil; DELATINNE, Jean-Pierre; ESCUDERO HERNANDEZ, Maria Luisa; PINILLA, Veronique
Patent: WO2011/161255 A2, 2011 ;
反应条件
1.1: potassium carbonate / 2-methyl tetrahydrofuran / Reflux 2.1: methyltretrahydrofuran, 2- / 75 °C 3.1: hydrogenchloride / water; tetrahydrofuran / 0.25 h / 65 °C 4.1: sodium hydrogensulfite; water; hydrogen bromide; acetic acid / 2 h / Reflux 5.1: sodium carbonate / o-xylene; water / 70 - 80 °C 5.2: Reflux 5.3: 15 - 55 °C 6.1: ammonia / cyclohexane; water / Reflux View Scheme
反应条件
(S)-(+)-N-(3,5-dinitrobenzoyl)-α-phenylglycine in water; acetonitrile T=0 - 5°C; 2 h;
参考文献
KANDULA, Mahesh
Patent: WO2013/168033 A1, 2013 ;
Location in patent: Paragraph 0099; 00100 ;
反应条件
1.1: potassium carbonate / 2-methyl tetrahydrofuran / Reflux 2.1: methyltretrahydrofuran, 2- / 75 °C 3.1: hydrogenchloride / water; tetrahydrofuran / 0.25 h / 65 °C 4.1: sodium hydrogensulfite; water; hydrogen bromide; acetic acid / 2 h / Reflux 5.1: sodium carbonate / o-xylene; water / 70 - 80 °C 5.2: Reflux 5.3: 15 - 55 °C View Scheme
参考文献
UCB PHARMA GMBH; ATES, Celal; SCHULE, Arnaud; PALACIO, Magali; DEUTSCH, Paul; VASSELIN, David; CARLY, Nicolas; PHADTARE, Ganesh; YERANDE, Swapnil; DELATINNE, Jean-Pierre; ESCUDERO HERNANDEZ, Maria Luisa; PINILLA, Veronique
Patent: WO2011/161255 A2, 2011 ;
反应条件
1: With sodium acetate; sodium tris(acetoxy)borohydride; acetic acid in tetrahydrofuran
T=0 - 10°C;
2: With sodium hydroxide in tetrahydrofuran; water
T=0 - 20°C; 0.5 h;
3: With hydrogenchloride in tetrahydrofuran; water
T=10 - 50°C; 1.33333 h;
参考文献
UCB PHARMA GMBH; Ates, Celal; Schule, Arnaud; Palacio, Magali; Deutsch, Paul; Vasselin, David; Carly, Nicolas; Phadtare, Ganesh; Yerande, Swapnil; Delatinne, Jean-Pierre; Escudero Hernandez, Maria Luisa; Pinilla, Veronique
Patent: US2013/102794 A1, 2013 ;
Location in patent: Paragraph 0189-0191 ;
反应条件
1: With lauryl mercaptan in ethyl acetate
Inert atmosphereReflux;
2: With 2,2'-azo-bisisobutyronitrile in ethyl acetate
0.583333 h; Inert atmosphereReflux;
3: With hydrogenchloride in water; ethyl acetate
0.0833333 h; Reflux;
参考文献
UCB PHARMA GMBH; Ates, Celal; Schule, Arnaud; Palacio, Magali; Deutsch, Paul; Vasselin, David; Carly, Nicolas; Phadtare, Ganesh; Yerande, Swapnil; Delatinne, Jean-Pierre; Escudero Hernandez, Maria Luisa; Pinilla, Veronique
Patent: US2013/102794 A1, 2013 ;
Location in patent: Paragraph 0238 ;
反应条件
1: With acetic acid in 1,2-dichloro-ethane
0.5 h; Inert atmosphere;
2: With sodium cyanoborohydride in methanol; 1,2-dichloro-ethane
T=20°C;
3: With hydrogenchloride in diethyl ether; ethyl acetate
参考文献
KANDULA, Mahesh
Patent: WO2013/168033 A1, 2013 ;
Location in patent: Paragraph 0097 ;
反应条件
hydrogenchloride in diethyl ether; ethyl acetate
参考文献
Ghoshs, Balaram; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.
Journal of Medicinal Chemistry, 2010 , vol. 53, # 5 p. 2114 - 2125
Title/Abstract Full Text View citing articles Show Details
Ghosh, Balaram; Antonio, Tamara; Gopishetty, Bhaskar; Reith, Maarten; Dutta, Aloke
Bioorganic and Medicinal Chemistry, 2010 , vol. 18, # 15 p. 5661 - 5674
反应条件
1: (S)-(+)-N-(3,5-dinitrobenzoyl)-α-phenylglycine / acetonitrile; water / 2 h / 0 - 5 °C
2: hydrogen bromide / acetic acid / 3 h / |Reflux
3: sodium hydroxide / water / 40 °C / pH 12.5
View Scheme
参考文献
KANDULA, Mahesh
Patent: WO2013/168033 A1, 2013 ;
反应条件
potassium carbonate in 2-methyl tetrahydrofuran
Reflux; Product distribution / selectivity;
参考文献
UCB PHARMA GMBH; Ates, Celal; Schule, Arnaud; Palacio, Magali; Deutsch, Paul; Vasselin, David; Carly, Nicolas; Phadtare, Ganesh; Yerande, Swapnil; Delatinne, Jean-Pierre; Escudero Hernandez, Maria Luisa; Pinilla, Veronique
Patent: US2013/102794 A1, 2013 ;
Location in patent: Paragraph 0199-0201 ;