DayangChem exported this product to many countries and regions at best price. If you are looking for the material's manufacturer or supplier in China, DayangChem is your best choice. Pls contact with us freely for getting detailed product spe
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inquiryNaratriptan CAS:121679-13-8 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediate
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inquiryNaratriptan CAS 121679-13-8 Purity: 99% Min Application: Intermediates Appearance: Powder Package: Bag Delivery: 3-5days Our Advantage & Service 1.Top quality: Using high quality material and establishing a strict quality control sys
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N-methyl-2-[1-benzyl-3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide
naratriptan
Conditions | Yield |
---|---|
With ammonia; sodium In tetrahydrofuran for 0.166667h; | 84% |
Stage #1: N-methyl-2-[1-benzyl-3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide With hydrogen; acetic acid; palladium 10% on activated carbon at 25℃; under 724.026 Torr; Stage #2: With ammonia In water at 10℃; pH=7.5 - 8.5; |
2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonic acid benzylmethylamide
naratriptan
Conditions | Yield |
---|---|
With sodium In tetrahydrofuran; ammonia at -78℃; for 0.75h; | 80% |
N-methyl-2-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]ethanesulfonamide
naratriptan
Conditions | Yield |
---|---|
With hydrogen; palladium 10% on activated carbon In ethanol at 25 - 35℃; Product distribution / selectivity; | 73.3% |
With hydrogen; palladium 10% on activated carbon In ethanol; N,N-dimethyl-formamide at 25 - 35℃; under 2206.72 Torr; for 2h; Product distribution / selectivity; | 72.7% |
With 5% Pd(II)/C(eggshell); hydrogen; acetic acid In methanol; water at 25 - 35℃; under 6840.46 - 7600.51 Torr; Reactivity; Reagent/catalyst; Solvent; Time; | 64% |
A
naratriptan
B
2-[3-(1-benzyl-piperidin-4-yl)-1H-indol-5-yl]-ethanesulfonic acid methylamide
Conditions | Yield |
---|---|
With lithium triamylborohydride In tetrahydrofuran for 26h; dequaternisation; Heating; | A n/a B 44% |
A
naratriptan
B
2-{3-[1-(1-phenyl-ethyl)-piperidin-4-yl]-1H-indol-5-yl}-ethanesulfonic acid methylamide
Conditions | Yield |
---|---|
With L-Selectride In tetrahydrofuran at 60℃; for 22h; dequaternisation; Title compound not separated from byproducts; |
2-(1-benzyl-1H-indol-5-yl)ethanesulfonic acid methylamide
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 2: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 3: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme | |
Multi-step reaction with 3 steps 1.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 2.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C 2.2: 25 - 30 °C 2.3: 10 - 15 °C 3.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr 3.2: 10 °C / pH 7.5 - 8.5 View Scheme | |
Multi-step reaction with 2 steps 1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 2: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C View Scheme |
2-(1-benzyl-1H-indol-5-yl)ethenesulfonic acid methylamide
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr 2: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 3: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 4: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme |
2-[1-benzyl-3-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indol-5-yl]-ethanesulfonic acid methylamide
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 2: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme | |
With triethylsilane; ethanol; hydrogen; palladium 10% on activated carbon In ethanol at 25 - 30℃; | |
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C 1.2: 25 - 30 °C 1.3: 10 - 15 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr 2.2: 10 °C / pH 7.5 - 8.5 View Scheme |
N-benzylindoline-5-carboxaldehyde
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 75 percent / DDQ / CH2Cl2 / 3 h / 0 °C 2.1: t-BuOK / tetrahydrofuran / 1 h / -78 °C 2.2: 73 percent / tetrahydrofuran / -78 - 0 °C 3.1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr 4.1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 5.1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 6.1: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme |
1-benzyl-1H-indole-5-carbaldehyde
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: t-BuOK / tetrahydrofuran / 1 h / -78 °C 1.2: 73 percent / tetrahydrofuran / -78 - 0 °C 2.1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr 3.1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 4.1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 5.1: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme |
1-Methyl-4-piperidone
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 83 percent / KOH / methanol / 8 h / Heating 2: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 3: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme |
trans-2-(p-nitrophenyl)ethenesulfonyl chloride
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C 2: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 3: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 4: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 5: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 6: 84 percent / KOH / methanol / 2 h / 20 °C 7: 83 percent / KOH / methanol / 8 h / Heating 8: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 9: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme |
4-nitrobenzaldehdye
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 13 steps 1: 86 percent / t-BuOK / tetrahydrofuran / 4.5 h / -78 °C 2: 82 percent / triethylamine; methanesulfonyl chloride / CHCl3 / 25.25 h / 0 - 5 °C 3: 0.7 g / NaI*2H2O / acetone / 6 h / Heating 4: 64 percent / dimethylformamide; SOCl2 / benzene / 5 h / Heating 5: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C 6: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 7: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 8: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 9: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 10: 84 percent / KOH / methanol / 2 h / 20 °C 11: 83 percent / KOH / methanol / 8 h / Heating 12: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 13: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme | |
Multi-step reaction with 10 steps 1: 100 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 2: 85 percent / triethylamine; methanesulfonyl chloride / CH2Cl2 / 24.17 h / 0 - 5 °C 3: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 4: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 5: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 6: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 7: 84 percent / KOH / methanol / 2 h / 20 °C 8: 83 percent / KOH / methanol / 8 h / Heating 9: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 10: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme |
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: 0.7 g / NaI*2H2O / acetone / 6 h / Heating 2: 64 percent / dimethylformamide; SOCl2 / benzene / 5 h / Heating 3: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C 4: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 5: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 6: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 7: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 8: 84 percent / KOH / methanol / 2 h / 20 °C 9: 83 percent / KOH / methanol / 8 h / Heating 10: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 11: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme |
2-hydroxy-2-(4-nitrophenyl)ethanesulfonic acid isopropyl ester
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1: 82 percent / triethylamine; methanesulfonyl chloride / CHCl3 / 25.25 h / 0 - 5 °C 2: 0.7 g / NaI*2H2O / acetone / 6 h / Heating 3: 64 percent / dimethylformamide; SOCl2 / benzene / 5 h / Heating 4: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C 5: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 6: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 7: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 8: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 9: 84 percent / KOH / methanol / 2 h / 20 °C 10: 83 percent / KOH / methanol / 8 h / Heating 11: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 12: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme |
2-(4-nitrophenyl)ethenesulfonic acid benzylmethylamide
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 2: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 3: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 4: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 5: 84 percent / KOH / methanol / 2 h / 20 °C 6: 83 percent / KOH / methanol / 8 h / Heating 7: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 8: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme |
2-(4-aminophenyl)ethanesulfonic acid benzylmethylamide
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 2: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 3: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 4: 84 percent / KOH / methanol / 2 h / 20 °C 5: 83 percent / KOH / methanol / 8 h / Heating 6: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 7: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme |
N-benzyl-2-(1H-indole-5-yl)-N-methylethane-1-sulfonamide
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 83 percent / KOH / methanol / 8 h / Heating 2: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 3: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme |
2-hydroxy-2-(4-nitrophenyl)ethanesulfonic acid benzylmethylamide
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 85 percent / triethylamine; methanesulfonyl chloride / CH2Cl2 / 24.17 h / 0 - 5 °C 2: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 3: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 4: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 5: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 6: 84 percent / KOH / methanol / 2 h / 20 °C 7: 83 percent / KOH / methanol / 8 h / Heating 8: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 9: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme |
2-[4-(2,2-dimethoxyethylamino)phenyl]ethanesulfonic acid benzylmethylamide
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 2: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 3: 84 percent / KOH / methanol / 2 h / 20 °C 4: 83 percent / KOH / methanol / 8 h / Heating 5: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 6: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme |
2-[1-(2,2,2-trifluoroacetyl)-1H-indol-5-yl]ethanesulfonic acid benzylmethylamide
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 84 percent / KOH / methanol / 2 h / 20 °C 2: 83 percent / KOH / methanol / 8 h / Heating 3: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 4: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme |
2-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]ethanesulfonic acid benzylmethylamide
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 2: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme |
N-{4-[2-(benzylmethylsulfamoyl)ethyl]phenyl}-N-(2,2-dimethoxyethyl)-2,2,2-trifluoroacetamide
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 2: 84 percent / KOH / methanol / 2 h / 20 °C 3: 83 percent / KOH / methanol / 8 h / Heating 4: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 5: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme |
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: 64 percent / dimethylformamide; SOCl2 / benzene / 5 h / Heating 2: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C 3: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 4: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 5: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 6: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 7: 84 percent / KOH / methanol / 2 h / 20 °C 8: 83 percent / KOH / methanol / 8 h / Heating 9: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 10: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme |
1-methyl-4 (formylmethyl)piperidine
naratriptan
Conditions | Yield |
---|---|
With hydrogenchloride; polyphosphate ester; sodium carbonate In chloroform; water |
2-(4-amino-phenyl)ethanesulfonic acid methylamide
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: sodium hydrogencarbonate; iodine / dichloromethane / 25 - 30 °C 2.1: dichloromethane / 1.5 h / 25 °C 3.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 3.2: 25 °C 4.1: potassium hydroxide; ethanol / 15 - 25 °C 5.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 5.2: 0.5 h / 25 °C 6.1: trifluoroacetic acid / ethanol / 25 °C / Reflux 6.2: 10 - 15 °C / pH 8 7.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 7.2: 10 °C / pH 7.5 - 8.5 View Scheme | |
Multi-step reaction with 6 steps 1.1: sodium hydrogencarbonate; iodine / dichloromethane / 25 - 30 °C 2.1: dichloromethane / 1.5 h / 25 °C 3.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 3.2: 25 °C 4.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 25 - 85 °C / Inert atmosphere 4.2: 0.5 h / 25 °C 5.1: trifluoroacetic acid / ethanol / 25 °C / Reflux 5.2: 10 - 15 °C / pH 8 6.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 6.2: 10 °C / pH 7.5 - 8.5 View Scheme | |
Multi-step reaction with 7 steps 1.1: sodium hydrogencarbonate; iodine / dichloromethane / 25 - 30 °C 2.1: methanol / 25 - 30 °C 2.2: 4 h / 25 - 30 °C 3.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 3.2: 25 °C 4.1: potassium hydroxide; ethanol / 15 - 25 °C 5.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 6.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 7.1: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: sodium hydrogencarbonate; iodine / dichloromethane / 25 - 30 °C 2.1: methanol / 25 - 30 °C 2.2: 4 h / 25 - 30 °C 3.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 3.2: 25 °C 4.1: potassium hydroxide; ethanol / 15 - 25 °C 5.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 6.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 7.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C 7.2: 25 - 30 °C 7.3: 10 - 15 °C 8.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr 8.2: 10 °C / pH 7.5 - 8.5 View Scheme |
N-Methyl-1H-indole-5-ethanesulphonamide
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / ethanol / 25 °C / Reflux 1.2: 10 - 15 °C / pH 8 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 2.2: 10 °C / pH 7.5 - 8.5 View Scheme |
N-[2-iodo-4-(2-(methylsulfamoyl)ethyl)phenyl]acetamide
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 1.2: 25 °C 2.1: potassium hydroxide; ethanol / 15 - 25 °C 3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 3.2: 0.5 h / 25 °C 4.1: trifluoroacetic acid / ethanol / 25 °C / Reflux 4.2: 10 - 15 °C / pH 8 5.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 5.2: 10 °C / pH 7.5 - 8.5 View Scheme | |
Multi-step reaction with 4 steps 1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 1.2: 25 °C 2.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 25 - 85 °C / Inert atmosphere 2.2: 0.5 h / 25 °C 3.1: trifluoroacetic acid / ethanol / 25 °C / Reflux 3.2: 10 - 15 °C / pH 8 4.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 4.2: 10 °C / pH 7.5 - 8.5 View Scheme |
2-(4-benzylamino-3-iodophenyl)ethanesulfonic acid methylamide
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 1.2: 25 °C 2.1: potassium hydroxide; ethanol / 15 - 25 °C 3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 4.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 5.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C 5.2: 25 - 30 °C 5.3: 10 - 15 °C 6.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr 6.2: 10 °C / pH 7.5 - 8.5 View Scheme | |
Multi-step reaction with 5 steps 1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 1.2: 25 °C 2.1: potassium hydroxide; ethanol / 15 - 25 °C 3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 4.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 5.1: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C View Scheme |
(1-bromoethyl)benzne
naratriptan
Conditions | Yield |
---|---|
In acetone at 50℃; for 260h; quaternisation; | 100% |
benzyl bromide
naratriptan
Conditions | Yield |
---|---|
In acetone quaternisation; | 99% |
Conditions | Yield |
---|---|
In acetone at 20℃; for 18h; quaternisation; | 95% |
naratriptan
naratriptan hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 0 - 30℃; for 1h; pH=1.0 - 1.5; Product distribution / selectivity; | 93.4% |
With hydrogenchloride In methanol; water at 0 - 10℃; | 84% |
With hydrogenchloride In methanol; ethanol at 5 - 25℃; pH=1.0; | 71.7% |
With hydrogenchloride In isopropyl alcohol; acetone at 5 - 10℃; pH=1; |
naratriptan
2-{3-[1-(1-phenyl-ethyl)-piperidin-4-yl]-1H-indol-5-yl}-ethanesulfonic acid methylamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 100 percent / acetone / 260 h / 50 °C 2: lithium tri-sec-butylborohydride / tetrahydrofuran / 22 h / 60 °C View Scheme | |
Multi-step reaction with 2 steps 1: 100 percent / acetone / 260 h / 50 °C 2: lithium trisecbutylborohydride / tetrahydrofuran / 70 h / Heating View Scheme |
naratriptan
2-[3-(1-benzyl-piperidin-4-yl)-1H-indol-5-yl]-ethanesulfonic acid methylamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 99 percent / acetone 2: 44 percent / lithium trisamylborohydride / tetrahydrofuran / 26 h / Heating View Scheme |
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