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CAS No.: | 290297-26-6 |
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Name: | 2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide |
Article Data: | 12 |
Molecular Structure: | |
Formula: | C30H32 F6 N4 O |
Molecular Weight: | 578.601 |
Synonyms: | 2-[3,5-Bis(trifluoromethyl)phenyl]-N-[6-(4-methylpiperazin-1-yl)-4-o-tolylpyridin-3-yl]-N-methylisobutyramide;Netupitant; Ro 67-31898/000 |
Density: | 1.255 |
Melting Point: | 156.2-160.0 °C |
Boiling Point: | 597.4°C at 760 mmHg |
Flash Point: | 315.1°C |
PSA: | 39.68000 |
LogP: | 6.78990 |
methyl-[6-(4-methyl-piperazin-1-yl)-4-o-tolyl-pyridin-3-yl]-amine
2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride
netupitant
Conditions | Yield |
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With sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 35 - 40℃; for 3h; Cooling with ice; | 81% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 35 - 40℃; for 3h; Cooling with ice; | 81% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 10℃; for 2h; | 74% |
1-methyl-piperazine
2-(3,5-bis(trifluoromethyl)phenyl)-N-(6-chloro-4-(o-tolyl)pyridin-3-yl)-N,2-dimethylpropanamide
netupitant
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane at 80℃; for 3h; | 80% |
methyl-[6-(4-methyl-piperazin-1-yl)-4-o-tolyl-pyridin-3-yl]-amine
netupitant
Conditions | Yield |
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With N-ethyl-N,N-diisopropylamine In dichloromethane Heating; |
1-methyl-piperazine
netupitant
Conditions | Yield |
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Multi-step reaction with 4 steps 1: 2 h / 100 °C 2: 99 percent / N-bromosuccinimide / CH2Cl2; methanol / 7 h / -5 °C 3: Red-Al / toluene; CH2Cl2 / 1 h / 50 °C 4: 13.5 g / i-Pr2NEt / CH2Cl2 / 3 h / 0 °C View Scheme |
netupitant
Conditions | Yield |
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Multi-step reaction with 5 steps 1: 7.8 g / NH3 / tetrahydrofuran; H2O / 0.5 h / 0 °C 2: 2 h / 100 °C 3: 99 percent / N-bromosuccinimide / CH2Cl2; methanol / 7 h / -5 °C 4: Red-Al / toluene; CH2Cl2 / 1 h / 50 °C 5: 13.5 g / i-Pr2NEt / CH2Cl2 / 3 h / 0 °C View Scheme |
6-chloro-4-(o-tolyl)nicotinamide
netupitant
Conditions | Yield |
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Multi-step reaction with 4 steps 1: 2 h / 100 °C 2: 99 percent / N-bromosuccinimide / CH2Cl2; methanol / 7 h / -5 °C 3: Red-Al / toluene; CH2Cl2 / 1 h / 50 °C 4: 13.5 g / i-Pr2NEt / CH2Cl2 / 3 h / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: 2 h / 100 °C 2.1: N-Bromosuccinimide / methanol; dichloromethane / 6 h / -5 °C 2.2: 5.33 h / 5 °C 3.1: dichloromethane; toluene / 2 h / 50 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 35 - 40 °C / Cooling with ice View Scheme | |
Multi-step reaction with 4 steps 1.1: 2 h / 100 °C 2.1: N-Bromosuccinimide / methanol; dichloromethane / 16 h / -5 °C 2.2: 5.3 h / -5 °C 3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / dichloromethane; toluene / 2 h / 50 °C 4.1: sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 35 - 40 °C / Cooling with ice View Scheme |
6-chloro-4-o-tolyl-nicotinic acid
netupitant
Conditions | Yield |
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Multi-step reaction with 6 steps 1: SOCl2; DMF / tetrahydrofuran / 2.5 h / 50 °C 2: 7.8 g / NH3 / tetrahydrofuran; H2O / 0.5 h / 0 °C 3: 2 h / 100 °C 4: 99 percent / N-bromosuccinimide / CH2Cl2; methanol / 7 h / -5 °C 5: Red-Al / toluene; CH2Cl2 / 1 h / 50 °C 6: 13.5 g / i-Pr2NEt / CH2Cl2 / 3 h / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: thionyl chloride / N,N-dimethyl-formamide / 2 h / 50 °C 1.2: 0.5 h / 0 °C 2.1: 2 h / 100 °C 3.1: N-Bromosuccinimide / methanol; dichloromethane / 6 h / -5 °C 3.2: 5.33 h / 5 °C 4.1: dichloromethane; toluene / 2 h / 50 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 35 - 40 °C / Cooling with ice View Scheme | |
Multi-step reaction with 5 steps 1.1: thionyl chloride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 50 °C 1.2: 0.5 h / 0 °C 2.1: 2 h / 100 °C 3.1: N-Bromosuccinimide / methanol; dichloromethane / 16 h / -5 °C 3.2: 5.3 h / -5 °C 4.1: sodium bis(2-methoxyethoxy)aluminium dihydride / dichloromethane; toluene / 2 h / 50 °C 5.1: sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 35 - 40 °C / Cooling with ice View Scheme |
N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide
netupitant
Conditions | Yield |
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Multi-step reaction with 5 steps 1: 4 h / 100 °C 2: MeSO3H / 5 h / 100 °C 3: 99 percent / N-bromosuccinimide / CH2Cl2; methanol / 7 h / -5 °C 4: Red-Al / toluene; CH2Cl2 / 1 h / 50 °C 5: 13.5 g / i-Pr2NEt / CH2Cl2 / 3 h / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1: 100 °C 2: methanesulfonic acid / 100 °C 3: N-Bromosuccinimide / dichloromethane / -5 °C 4: RedAl / toluene / 50 °C 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 40 °C View Scheme |
4-(2-methylphenyl)-6-(4-methylpiperazinyl)-3-pyridinecarboxamide
netupitant
Conditions | Yield |
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Multi-step reaction with 3 steps 1: 99 percent / N-bromosuccinimide / CH2Cl2; methanol / 7 h / -5 °C 2: Red-Al / toluene; CH2Cl2 / 1 h / 50 °C 3: 13.5 g / i-Pr2NEt / CH2Cl2 / 3 h / 0 °C View Scheme | |
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / dichloromethane / -5 °C 2: RedAl / toluene / 50 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 40 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / methanol; dichloromethane / 6 h / -5 °C 1.2: 5.33 h / 5 °C 2.1: dichloromethane; toluene / 2 h / 50 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 35 - 40 °C / Cooling with ice View Scheme | |
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / methanol; dichloromethane / 16 h / -5 °C 1.2: 5.3 h / -5 °C 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / dichloromethane; toluene / 2 h / 50 °C 3.1: sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 35 - 40 °C / Cooling with ice View Scheme |
[6-(4-methyl-piperazin-1-yl)-4-o-tolylpyridin-3-yl]-carbamic acid methyl ester
netupitant
Conditions | Yield |
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Multi-step reaction with 2 steps 1: Red-Al / toluene; CH2Cl2 / 1 h / 50 °C 2: 13.5 g / i-Pr2NEt / CH2Cl2 / 3 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: RedAl / toluene / 50 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 40 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium bis(2-methoxyethoxy)aluminium dihydride / dichloromethane; toluene / 2 h / 50 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 35 - 40 °C View Scheme | |
Multi-step reaction with 2 steps 1: dichloromethane; toluene / 2 h / 50 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 35 - 40 °C / Cooling with ice View Scheme | |
Multi-step reaction with 2 steps 1: sodium bis(2-methoxyethoxy)aluminium dihydride / dichloromethane; toluene / 2 h / 50 °C 2: sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 35 - 40 °C / Cooling with ice View Scheme |