MOP-21826
tolvaptan
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate at 0℃; for 2h; | 96% |
With methanol; sodium tetrahydroborate at 20℃; for 5h; | 94% |
With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran at -5 - 20℃; Solvent; | 94.2% |
MOP-21826
E
tolvaptan
Conditions | Yield |
---|---|
Stage #1: MOP-21826 With sodium tetrahydroborate In methanol for 1h; Stage #2: With hydrogenchloride In methanol; water at 20℃; | A n/a B n/a C n/a D n/a E 90% |
2-methyl-4-(2-methylbenzoylamino)benzoic acid chloride
tolvaptan
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine In N,N-dimethyl acetamide; water at 0℃; for 2h; Reagent/catalyst; | 72% |
tolvaptan
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 50℃; for 2h; | |
With sodium hydroxide; ethanol; water at 50℃; for 2h; |
(rac)-7-chloro-4-oxo-1,2,3,4-tetrahydronaphthalen-1-yl pivalate
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 96 percent / hydroxylamine hydrochloride; sodium acetate / ethanol; H2O / 2 h / Heating 2: PCl5 / CH2Cl2 / 2 h / 20 °C 3: acetic acid; Zn / 0.5 h / Heating 4: BH3*THF / tetrahydrofuran / 0.5 h / Heating 5: 98 percent / triethylamine / CH2Cl2 / 1 h / 20 °C 6: 82 percent / hydrochloric acid; SnCl2 / ethanol / 2 h / Heating 7: triethylamine / CH2Cl2 / 1 h / 20 °C 8: NaOH / ethanol; H2O / 2 h / 50 °C View Scheme |
2,2-dimethylpropionic acid 7-chloro-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl ester
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 98 percent / triethylamine / CH2Cl2 / 1 h / 20 °C 2: 82 percent / hydrochloric acid; SnCl2 / ethanol / 2 h / Heating 3: triethylamine / CH2Cl2 / 1 h / 20 °C 4: NaOH / ethanol; H2O / 2 h / 50 °C View Scheme |
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: BH3*THF / tetrahydrofuran / 0.5 h / Heating 2: 98 percent / triethylamine / CH2Cl2 / 1 h / 20 °C 3: 82 percent / hydrochloric acid; SnCl2 / ethanol / 2 h / Heating 4: triethylamine / CH2Cl2 / 1 h / 20 °C 5: NaOH / ethanol; H2O / 2 h / 50 °C View Scheme |
2,2-dimethylpropionic acid 4-[(E)-hydroxyimino]-7-chloro-1,2,3,4-tetrahydronaphthalen-1-yl ester
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: PCl5 / CH2Cl2 / 2 h / 20 °C 2: acetic acid; Zn / 0.5 h / Heating 3: BH3*THF / tetrahydrofuran / 0.5 h / Heating 4: 98 percent / triethylamine / CH2Cl2 / 1 h / 20 °C 5: 82 percent / hydrochloric acid; SnCl2 / ethanol / 2 h / Heating 6: triethylamine / CH2Cl2 / 1 h / 20 °C 7: NaOH / ethanol; H2O / 2 h / 50 °C View Scheme |
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: acetic acid; Zn / 0.5 h / Heating 2: BH3*THF / tetrahydrofuran / 0.5 h / Heating 3: 98 percent / triethylamine / CH2Cl2 / 1 h / 20 °C 4: 82 percent / hydrochloric acid; SnCl2 / ethanol / 2 h / Heating 5: triethylamine / CH2Cl2 / 1 h / 20 °C 6: NaOH / ethanol; H2O / 2 h / 50 °C View Scheme |
2,2-dimethylpropionic acid 7-chloro-1-(4-amino-2-methylbenzoyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl ester
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / CH2Cl2 / 1 h / 20 °C 2: NaOH / ethanol; H2O / 2 h / 50 °C View Scheme |
2,2-dimethylpropionic acid 7-chloro-1-(2-methyl-4-nitrobenzoyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl ester
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 82 percent / hydrochloric acid; SnCl2 / ethanol / 2 h / Heating 2: triethylamine / CH2Cl2 / 1 h / 20 °C 3: NaOH / ethanol; H2O / 2 h / 50 °C View Scheme |
4-chlorobenzenesulfonyl chloride
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: 85 percent / pyridine / 20 °C 2.1: 94 percent / K2CO3 / dimethylformamide / 4 h / 120 °C 3.1: t-BuOK / toluene / 0.5 h / Heating 3.2: 60 percent / conc. HCl / acetic acid / 5 h / Heating 4.1: 81 percent / polyphosphoric acid / 1.5 h / 80 - 100 °C 5.1: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C 6.1: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C 7.1: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C 8.1: 30 percent / NaBH4 / methanol / 1 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1: sodium carbonate / acetonitrile / 5 h / 80 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C 3: potassium tert-butylate / toluene / 1 h / 120 °C 4: acetic acid; hydrogenchloride / water / 6 h / 100 °C 5: hydrogenchloride; tin(II) chloride dihdyrate / ethanol / 4 h / 20 °C 6: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C 7: sodium tetrahydroborate; methanol / 2 h / 0 °C View Scheme |
5-chloro-2-nitrobenzoic acid
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: 100 percent / K2CO3 / acetone / 0.5 h / Heating 2.1: SnCl2*2H2O; conc. HCl / ethanol / 20 °C 3.1: 85 percent / pyridine / 20 °C 4.1: 94 percent / K2CO3 / dimethylformamide / 4 h / 120 °C 5.1: t-BuOK / toluene / 0.5 h / Heating 5.2: 60 percent / conc. HCl / acetic acid / 5 h / Heating 6.1: 81 percent / polyphosphoric acid / 1.5 h / 80 - 100 °C 7.1: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C 8.1: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C 9.1: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C 10.1: 30 percent / NaBH4 / methanol / 1 h / 20 °C View Scheme |
2-methyl-4-nitrobenzoyl chloride
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C 2: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C 3: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C 4: 30 percent / NaBH4 / methanol / 1 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate / dichloromethane; water / pH 7 - 8 2.1: tin(ll) chloride / methanol / 16 h / 20 °C 3.1: sodium hydrogencarbonate / dichloromethane / 0 - 5 °C / pH 7 - 8 4.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 4.2: pH 6 - 7 View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate / water; dichloromethane / 0 - 5 °C / pH 7.0 - 8.0 2.1: tin(IV) chloride / methanol / 16 h / 20 °C 3.1: sodium hydrogencarbonate / water; dichloromethane / 0 - 5 °C / pH 7.0 - 8.0 4.1: sodium tetrahydroborate / methanol / 1 h / 20 °C 4.2: pH 6.0 - 7.0 View Scheme | |
Multi-step reaction with 4 steps 1.1: magnesium hydroxide / acetonitrile / 0.5 h / 10 °C 1.2: 5 h 2.1: methanol; tin(II) chloride dihdyrate / 23 h / 10 °C 3.1: magnesium hydroxide / dichloromethane; water / 0.5 h / 10 °C 3.2: 3 h 4.1: sodium tetrahydroborate; methanol / 1 h View Scheme |
2-methyl-4-nitrobenzoic acid
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: SOCl2 2: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C 3: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C 4: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C 5: 30 percent / NaBH4 / methanol / 1 h / 20 °C View Scheme |
methyl 5-chloro-2-nitrobenzoate
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: SnCl2*2H2O; conc. HCl / ethanol / 20 °C 2.1: 85 percent / pyridine / 20 °C 3.1: 94 percent / K2CO3 / dimethylformamide / 4 h / 120 °C 4.1: t-BuOK / toluene / 0.5 h / Heating 4.2: 60 percent / conc. HCl / acetic acid / 5 h / Heating 5.1: 81 percent / polyphosphoric acid / 1.5 h / 80 - 100 °C 6.1: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C 7.1: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C 8.1: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C 9.1: 30 percent / NaBH4 / methanol / 1 h / 20 °C View Scheme |
7-chloro-1,2,3,4-tetrahydro-5H-benzo[b]azepin-5-one
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C 2: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C 3: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C 4: 30 percent / NaBH4 / methanol / 1 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate / dichloromethane; water / pH 7 - 8 2.1: tin(ll) chloride / methanol / 16 h / 20 °C 3.1: sodium hydrogencarbonate / dichloromethane / 0 - 5 °C / pH 7 - 8 4.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 4.2: pH 6 - 7 View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate / water; dichloromethane / 0 - 5 °C / pH 7.0 - 8.0 2.1: tin(IV) chloride / methanol / 16 h / 20 °C 3.1: sodium hydrogencarbonate / water; dichloromethane / 0 - 5 °C / pH 7.0 - 8.0 4.1: sodium tetrahydroborate / methanol / 1 h / 20 °C 4.2: pH 6.0 - 7.0 View Scheme | |
Multi-step reaction with 4 steps 1: potassium carbonate; triphenylphosphine; palladium diacetate / N,N-dimethyl-formamide; water / 8 h / 120 °C / 22502.3 Torr / Autoclave 2: iron; ammonium chloride / water; methanol / 6 h / 35 - 40 °C 3: pyridine / dichloromethane / 2 h / 0 - 10 °C 4: sodium tetrahydroborate; methanol / 1 h / 15 - 30 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: magnesium hydroxide / acetonitrile / 0.5 h / 10 °C 1.2: 5 h 2.1: methanol; tin(II) chloride dihdyrate / 23 h / 10 °C 3.1: magnesium hydroxide / dichloromethane; water / 0.5 h / 10 °C 3.2: 3 h 4.1: sodium tetrahydroborate; methanol / 1 h View Scheme |
N-p-toluenesulfonyl-5-chloro-anthranilic acid methyl ester
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 94 percent / K2CO3 / dimethylformamide / 4 h / 120 °C 2.1: t-BuOK / toluene / 0.5 h / Heating 2.2: 60 percent / conc. HCl / acetic acid / 5 h / Heating 3.1: 81 percent / polyphosphoric acid / 1.5 h / 80 - 100 °C 4.1: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C 5.1: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C 6.1: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C 7.1: 30 percent / NaBH4 / methanol / 1 h / 20 °C View Scheme |
7-chloro-1-(4-methylbenzenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 81 percent / polyphosphoric acid / 1.5 h / 80 - 100 °C 2: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C 3: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C 4: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C 5: 30 percent / NaBH4 / methanol / 1 h / 20 °C View Scheme |
1-(4-amino-2-methylbenzoyl)-7-chloro-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C 2: 30 percent / NaBH4 / methanol / 1 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / water; dichloromethane / 0 - 5 °C / pH 7.0 - 8.0 2.1: sodium tetrahydroborate / methanol / 1 h / 20 °C 2.2: pH 6.0 - 7.0 View Scheme |
1-(4-nitro-2-methylbenzoyl)-7-chloro-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C 2: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C 3: 30 percent / NaBH4 / methanol / 1 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: tin(ll) chloride / methanol / 16 h / 20 °C 2.1: sodium hydrogencarbonate / dichloromethane / 0 - 5 °C / pH 7 - 8 3.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 3.2: pH 6 - 7 View Scheme | |
Multi-step reaction with 3 steps 1.1: tin(IV) chloride / methanol / 16 h / 20 °C 2.1: sodium hydrogencarbonate / water; dichloromethane / 0 - 5 °C / pH 7.0 - 8.0 3.1: sodium tetrahydroborate / methanol / 1 h / 20 °C 3.2: pH 6.0 - 7.0 View Scheme |
methyl 5-chloro-2-[N-(3-ethoxycarbonyl)propyl-N-p-toluenesulfonyl]aminobenzoate
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: t-BuOK / toluene / 0.5 h / Heating 1.2: 60 percent / conc. HCl / acetic acid / 5 h / Heating 2.1: 81 percent / polyphosphoric acid / 1.5 h / 80 - 100 °C 3.1: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C 4.1: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C 5.1: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C 6.1: 30 percent / NaBH4 / methanol / 1 h / 20 °C View Scheme |
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C 2: potassium tert-butylate / toluene / 1 h / 120 °C 3: acetic acid; hydrogenchloride / water / 6 h / 100 °C 4: hydrogenchloride; tin(II) chloride dihdyrate / ethanol / 4 h / 20 °C 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C 6: sodium tetrahydroborate; methanol / 2 h / 0 °C View Scheme |
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: potassium tert-butylate / toluene / 1 h / 120 °C 2: acetic acid; hydrogenchloride / water / 6 h / 100 °C 3: hydrogenchloride; tin(II) chloride dihdyrate / ethanol / 4 h / 20 °C 4: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C 5: sodium tetrahydroborate; methanol / 2 h / 0 °C View Scheme |
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: acetic acid; hydrogenchloride / water / 6 h / 100 °C 2: hydrogenchloride; tin(II) chloride dihdyrate / ethanol / 4 h / 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C 4: sodium tetrahydroborate; methanol / 2 h / 0 °C View Scheme |
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: dichloromethane / 4.5 h / 20 °C / Reflux 2: hydrogenchloride; tin(II) chloride dihdyrate / water; ethanol / 3 h / 20 °C 3: triethylamine / dichloromethane / 2.25 h / 20 °C 4: sodium tetrahydroborate; methanol / 5 h / 20 °C View Scheme |
4-chloro-aniline
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: sodium carbonate / acetonitrile / 4 h / 80 °C 2: triethylamine / dichloromethane / 3 h / 20 °C 3: sodium hydroxide / 1.5 h / 50 °C 4: thionyl chloride / dichloromethane / 2 h / 20 °C / Reflux 5: dichloromethane / 4.5 h / 20 °C / Reflux 6: hydrogenchloride; tin(II) chloride dihdyrate / water; ethanol / 3 h / 20 °C 7: triethylamine / dichloromethane / 2.25 h / 20 °C 8: sodium tetrahydroborate; methanol / 5 h / 20 °C View Scheme |
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: triethylamine / dichloromethane / 3 h / 20 °C 2: sodium hydroxide / 1.5 h / 50 °C 3: thionyl chloride / dichloromethane / 2 h / 20 °C / Reflux 4: dichloromethane / 4.5 h / 20 °C / Reflux 5: hydrogenchloride; tin(II) chloride dihdyrate / water; ethanol / 3 h / 20 °C 6: triethylamine / dichloromethane / 2.25 h / 20 °C 7: sodium tetrahydroborate; methanol / 5 h / 20 °C View Scheme |
tolvaptan
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: sodium hydroxide / 1.5 h / 50 °C 2: thionyl chloride / dichloromethane / 2 h / 20 °C / Reflux 3: dichloromethane / 4.5 h / 20 °C / Reflux 4: hydrogenchloride; tin(II) chloride dihdyrate / water; ethanol / 3 h / 20 °C 5: triethylamine / dichloromethane / 2.25 h / 20 °C 6: sodium tetrahydroborate; methanol / 5 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
Stage #1: Dibenzyl N,N-diisopropylphosphoramidite; tolvaptan With 1H-tetrazole In dichloromethane at 20℃; for 2h; Stage #2: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -40 - 0℃; for 1h; | 97.2% |
Multi-step reaction with 2 steps 1: 2H-tetrazole / dichloromethane / 2 h / 20 °C 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -40 - 0 °C View Scheme |
tolvaptan
C26H26ClN2O6P
Conditions | Yield |
---|---|
Stage #1: tolvaptan With triethylamine; trichlorophosphate In 1,2-dimethoxyethane at -15 - -12℃; for 2h; Stage #2: With sodium hydroxide; water In 1,2-dimethoxyethane; toluene at 0 - 50℃; Stage #3: With hydrogenchloride; water at 10℃; Product distribution / selectivity; | 97% |
Multi-step reaction with 3 steps 1: 2H-tetrazole / dichloromethane / 2 h / 20 °C 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -40 - 0 °C 3: 5%-palladium/activated carbon; hydrogen / ethanol / 0.17 h View Scheme | |
Multi-step reaction with 2 steps 1.1: 1H-tetrazole / dichloromethane / 2 h / 20 °C 1.2: 1 h / -40 - 0 °C 2.1: 5%-palladium/activated carbon; hydrogen / ethanol View Scheme |
Conditions | Yield |
---|---|
Stage #1: tolvaptan With pyridine; diphenyl hydrogen phosphite at 0 - 20℃; for 0.5h; Stage #2: methanol at 20℃; for 0.5h; | 91% |
tolvaptan
Conditions | Yield |
---|---|
With 1,3-bis(2,6-diisopropylphenyl)-2-fluoroimidazolium tetrafluoroborate; cesium fluoride In toluene at 80℃; for 17h; Inert atmosphere; Schlenk technique; Sealed tube; | 86% |
tolvaptan
Conditions | Yield |
---|---|
Stage #1: tolvaptan With triethylamine; trichlorophosphate In 1,2-dimethoxyethane at -18 - -13℃; for 2h; Inert atmosphere; Large scale; Stage #2: With water; sodium hydroxide In 1,2-dimethoxyethane at -3 - 30℃; for 0.5h; Inert atmosphere; Large scale; | 86% |
Multi-step reaction with 4 steps 1: 2H-tetrazole / dichloromethane / 2 h / 20 °C 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -40 - 0 °C 3: 5%-palladium/activated carbon; hydrogen / ethanol / 0.17 h 4: sodium hydroxide / methanol; water / 0.08 h / Cooling with ice View Scheme | |
Multi-step reaction with 3 steps 1.1: 1H-tetrazole / dichloromethane / 2 h / 20 °C 1.2: 1 h / -40 - 0 °C 2.1: 5%-palladium/activated carbon; hydrogen / ethanol 3.1: sodium hydroxide / methanol; water / 0.08 h / Cooling with ice View Scheme |
Conditions | Yield |
---|---|
Stage #1: tolvaptan With pyridine; diphenyl hydrogen phosphite at 20℃; for 0.5h; Stage #2: 3-Hydroxypropionitrile at 20℃; for 0.5h; | 75% |
tolvaptan
n-hexadecanoyl chloride
{7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl} hexadecanoate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; | 74% |
tolvaptan
Conditions | Yield |
---|---|
Stage #1: tolvaptan With triethylamine; phosphorus trichloride In tetrahydrofuran at -10℃; for 2h; Stage #2: With sodium hydroxide; water In tetrahydrofuran at 0℃; Product distribution / selectivity; | 60% |
Stage #1: tolvaptan With pyridine; diphenyl hydrogen phosphite at 20℃; for 1h; Stage #2: With water at 20℃; for 0.5h; Product distribution / selectivity; | 24% |
Conditions | Yield |
---|---|
Stage #1: tolvaptan With pyridine; diphenyl hydrogen phosphite at 0 - 20℃; for 1h; Stage #2: ethanol at 20℃; for 0.5h; | 38% |
Conditions | Yield |
---|---|
Stage #1: tolvaptan With triethylamine; trichlorophosphate In tetrahydrofuran for 0.5h; Cooling with ice/methanol; Stage #2: methanol With triethylamine In tetrahydrofuran for 0.5h; | 33% |
Conditions | Yield |
---|---|
Stage #1: tolvaptan With pyridine; diphenyl hydrogen phosphite at 20℃; for 1h; Stage #2: glycolic acid methyl ester at 20℃; for 12h; | 20% |
1. Introduction of Tolvaptan
Tolvaptan, with the IUPAC Name of N-[4-(7-chloro-5-hydroxy-2,3,4,5-tetrahydro-1-benzazepine-1-carbonyl)-3-methylphenyl]-2-methylbenzamide, is one kind of white powder. This chemical belongs to the Classification Code which include Treatment of congestive heart failure and hyponatremia [vasopressin V2 receptor antagonist]; Vasopressin V2 Receptor Antagonist.
2. Properties of Tolvaptan
Tolvaptan has the following properties: (1)Freely Rotating Bonds: 4; (2)Polar Surface Area: 49.85; (3)Index of Refraction: 1.663; (4)Molar Refractivity: 126.96 cm3; (5)Molar Volume: 342.4 cm3; (6)Surface Tension: 59.7 dyne/cm; (7)Density: 1.311 g/cm3; (8)Flash Point: 313.3 °C; (9)Enthalpy of Vaporization: 93.18 kJ/mol; (10)Boiling Point: 594.4 °C at 760 mmHg; (11)Vapour Pressure: 5.64E-15 mmHg at 25°C.
3. Structure Descriptors of Tolvaptan
You could convert the following datas into the molecular structure:
(1).Smiles:c1cc(c(cc1)C)C(=O)Nc1ccc(C(=O)N2CCC[C@@H](c3c2ccc(c3)Cl)O)c(c1)C
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