Conditions | Yield |
---|---|
In isopropyl alcohol for 1h; Reflux; | 98% |
In toluene; acetonitrile at 40 - 80℃; Product distribution / selectivity; | 86.2% |
In isopropyl alcohol at 5 - 10℃; for 0.5h; | 83% |
methanesulfonic acid
rasagiline mesylate
Conditions | Yield |
---|---|
Stage #1: (1R)-N-(prop-2-ynyl)-2,3-dihydro-1H-inden-1-amine hemihydrate With potassium carbonate In water pH=Ca. 10; Large scale; Stage #2: methanesulfonic acid In isopropyl alcohol at 20℃; for 1.5h; Large scale; | 92.6% |
methanesulfonic acid
rasagiline mesylate
Conditions | Yield |
---|---|
Stage #1: (1R)-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine L-(+)-tartrate With sodium hydrogencarbonate In water; ethyl acetate at 20 - 25℃; Inert atmosphere; Stage #2: methanesulfonic acid In isopropyl alcohol Reflux; | 89% |
Conditions | Yield |
---|---|
In isopropyl alcohol at 5℃; for 1.5h; Reflux; | 83% |
Conditions | Yield |
---|---|
In isopropyl alcohol at 5 - 10℃; for 0.75h; | 83% |
methanesulfonic acid
N-(2,3 dibromopropyl)-1-aminoindan
rasagiline mesylate
Conditions | Yield |
---|---|
Stage #1: N-(2,3 dibromopropyl)-1-aminoindan With potassium hydroxide In denaturated industrial spirit; water at 80 - 90℃; for 5h; Stage #2: methanesulfonic acid In isopropyl alcohol at 25 - 30℃; |
methanesulfonic acid
rasagiline mesylate
Conditions | Yield |
---|---|
In acetone for 0.75h; Product distribution / selectivity; Reflux; | n/a |
2,3-dihydro-1H-inden-1-amine
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 24 h / 55 °C 2.1: isopropyl alcohol / 1.5 h / 25 - 30 °C / Reflux 3.1: ammonia / water / pH ~ 8.5 - 9 3.2: 2 h / 25 - 30 °C View Scheme | |
Multi-step reaction with 4 steps 1: potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide / 7 h / 40 - 70 °C 2: 0.75 h / 25 - 65 °C 3: sodium hydroxide / water / 20 °C 4: acetone / 1 h / 25 - 35 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide / 7 h / 40 - 70 °C 2.1: 0.75 h / 25 - 65 °C 3.1: sodium hydroxide / water / 20 °C 4.1: hydrogen bromide / 0.5 h / 25 - 65 °C 5.1: sodium hydroxide / ethyl acetate / 4 h / 65 °C 5.2: 0.5 h / 40 °C View Scheme | |
Multi-step reaction with 4 steps 1: Candida antarctica lipase B; Pd/AlO(OH); potassium carbonate / toluene / 12 h / 50 °C / Resolution of racemate; Inert atmosphere; Schlenk technique; Enzymatic reaction 2: triethanolamine; sodium hydroxide / water / 6.25 h / 80 °C / Reflux 3: potassium carbonate / acetonitrile / 12 h / 30 °C / Reflux 4: isopropyl alcohol / 0.5 h / 5 - 10 °C View Scheme | |
Multi-step reaction with 6 steps 1: ethanol; tert-butyl methyl ether / 20 °C 2: ethanol / 2.32 h / 79 °C 3: sodium hydroxide / ethyl acetate / 0.5 h / 20 °C 4: hydrogenchloride / isopropyl alcohol / 0.5 h / 5 - 20 °C / Inert atmosphere 5: sodium hydroxide / toluene / 29 h / 30 °C 6: isopropyl alcohol / 1 h / 55 - 80 °C View Scheme |
methanesulfonic acid
(1R)-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine L-(+)-tartrate
rasagiline mesylate
Conditions | Yield |
---|---|
Stage #1: (1R)-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine L-(+)-tartrate With ammonia In water pH=~ 8.5 - 9; Stage #2: methanesulfonic acid In acetone at 25 - 30℃; for 2h; Product distribution / selectivity; |
inden-1-one
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: ethanol / 8 h / 25 - 30 °C 2.1: ethanol; sodium tetrahydroborate / 8 h / 25 - 30 °C 3.1: isopropyl alcohol / 1.5 h / 25 - 30 °C / Reflux 4.1: ammonia / water / pH ~ 8.5 - 9 4.2: 2 h / 25 - 30 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / tert-butyl methyl ether / 8 h 1.2: 1 h / -70 - -30 °C 2.1: diisobutylaluminium hydride / toluene; hexane / 1 h / -70 - -30 °C 2.2: 1 h / 20 °C 3.1: tert-butyl methyl ether / 21 h / 10 °C / Heating 4.1: sodium hydroxide 5.1: isopropyl alcohol / 16 h / 20 - 75 °C View Scheme | |
Multi-step reaction with 6 steps 1: hydroxylamine hydrochloride; sodium hydroxide / water; methanol / 70 - 75 °C 2: hydrogen; ammonia / Raney nickel / methanol / 10 - 42 °C / Autoclave 3: potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide / 7 h / 40 - 70 °C 4: 0.75 h / 25 - 65 °C 5: sodium hydroxide / water / 20 °C 6: acetone / 1 h / 25 - 35 °C View Scheme |
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: ethanol; sodium tetrahydroborate / 8 h / 25 - 30 °C 2.1: isopropyl alcohol / 1.5 h / 25 - 30 °C / Reflux 3.1: ammonia / water / pH ~ 8.5 - 9 3.2: 2 h / 25 - 30 °C View Scheme |
rasagiline
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogen bromide / 0.5 h / 25 - 65 °C 2.1: sodium hydroxide / ethyl acetate / 4 h / 65 °C 2.2: 0.5 h / 40 °C View Scheme |
N-propargyl-1-aminoindan
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: tert-butyl methyl ether / 21 h / 10 °C / Heating 2: sodium hydroxide 3: isopropyl alcohol / 16 h / 20 - 75 °C View Scheme | |
Multi-step reaction with 3 steps 1: 0.75 h / 25 - 65 °C 2: sodium hydroxide / water / 20 °C 3: acetone / 1 h / 25 - 35 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: 0.75 h / 25 - 65 °C 2.1: sodium hydroxide / water / 20 °C 3.1: hydrogen bromide / 0.5 h / 25 - 65 °C 4.1: sodium hydroxide / ethyl acetate / 4 h / 65 °C 4.2: 0.5 h / 40 °C View Scheme |
N-(2,3-dihydroinden-1-ylidene)prop-2-yn-1-amine
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: diisobutylaluminium hydride / toluene; hexane / 1 h / -70 - -30 °C 1.2: 1 h / 20 °C 2.1: tert-butyl methyl ether / 21 h / 10 °C / Heating 3.1: sodium hydroxide 4.1: isopropyl alcohol / 16 h / 20 - 75 °C View Scheme |
R-(+)-N-propargyl-1-aminoindane L-(+)-mandelate
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide 2: isopropyl alcohol / 16 h / 20 - 75 °C View Scheme |
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydroxide; tetrabutylammomium bromide / water / 0.25 h / 15 - 20 °C 1.2: 2.75 h / 15 - 20 °C 2.1: isopropyl alcohol / 0.5 h / 5 - 10 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: pyridine / dichloromethane / 0.58 h / 20 °C / Ice bath 2.1: caesium carbonate / acetonitrile / 0.17 h / 30 - 35 °C 2.2: 4 h / 30 - 35 °C 3.1: potassium hydroxide / water; methanol / 30 - 35 °C 4.1: isopropyl alcohol / 20 - 60 °C 4.2: 0.42 h / 20 - 60 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydroxide; tetrabutylammomium bromide / water / 0.25 h / 15 - 20 °C 1.2: 2.75 h / 15 - 20 °C 2.1: isopropyl alcohol / 0.5 h / 5 - 10 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium hydroxide / toluene / 29 h / 30 °C 2: isopropyl alcohol / 1 h / 55 - 80 °C View Scheme |
N-trifluoroacetyl-(R)-1-aminoindan
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: caesium carbonate / acetonitrile / 0.17 h / 30 - 35 °C 1.2: 4 h / 30 - 35 °C 2.1: potassium hydroxide / water; methanol / 30 - 35 °C 3.1: isopropyl alcohol / 20 - 60 °C 3.2: 0.42 h / 20 - 60 °C View Scheme | |
Multi-step reaction with 3 steps 1: caesium carbonate / acetonitrile; toluene / 30 - 35 °C 2: potassium hydroxide; water / methanol / 0.5 h / 30 - 35 °C 3: isopropyl alcohol / 50 - 60 °C View Scheme |
methanesulfonic acid
(1R)-2,3-dihydro-N-2-propynyl-1H-indane-1-amine hydrobromide
rasagiline mesylate
Conditions | Yield |
---|---|
Stage #1: (1R)-2,3-dihydro-N-2-propynyl-1H-indane-1-amine hydrobromide With sodium hydroxide In ethyl acetate at 65℃; for 4h; Stage #2: methanesulfonic acid In ethyl acetate at 40℃; for 0.5h; |
indan-1-one oxime
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: hydrogen; ammonia / Raney nickel / methanol / 10 - 42 °C / Autoclave 2: potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide / 7 h / 40 - 70 °C 3: 0.75 h / 25 - 65 °C 4: sodium hydroxide / water / 20 °C 5: acetone / 1 h / 25 - 35 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: hydrogen; ammonia / Raney nickel / methanol / 10 - 42 °C / Autoclave 2.1: potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide / 7 h / 40 - 70 °C 3.1: 0.75 h / 25 - 65 °C 4.1: sodium hydroxide / water / 20 °C 5.1: hydrogen bromide / 0.5 h / 25 - 65 °C 6.1: sodium hydroxide / ethyl acetate / 4 h / 65 °C 6.2: 0.5 h / 40 °C View Scheme | |
Multi-step reaction with 5 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 70 °C 2: Candida antarctica lipase B; Pd/AlO(OH); potassium carbonate / toluene / 12 h / 50 °C / Resolution of racemate; Inert atmosphere; Schlenk technique; Enzymatic reaction 3: triethanolamine; sodium hydroxide / water / 6.25 h / 80 °C / Reflux 4: potassium carbonate / acetonitrile / 12 h / 30 °C / Reflux 5: isopropyl alcohol / 0.5 h / 5 - 10 °C View Scheme | |
Multi-step reaction with 7 steps 1: ammonia; hydrogen / methanol / 20 h / 42 °C / 2625.26 Torr 2: ethanol; tert-butyl methyl ether / 20 °C 3: ethanol / 2.32 h / 79 °C 4: sodium hydroxide / ethyl acetate / 0.5 h / 20 °C 5: hydrogenchloride / isopropyl alcohol / 0.5 h / 5 - 20 °C / Inert atmosphere 6: sodium hydroxide / toluene / 29 h / 30 °C 7: isopropyl alcohol / 1 h / 55 - 80 °C View Scheme |
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / 20 °C 2.1: hydrogen bromide / 0.5 h / 25 - 65 °C 3.1: sodium hydroxide / ethyl acetate / 4 h / 65 °C 3.2: 0.5 h / 40 °C View Scheme |
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethanolamine; sodium hydroxide / water / 6.25 h / 80 °C / Reflux 2: potassium carbonate / acetonitrile / 12 h / 30 °C / Reflux 3: isopropyl alcohol / 0.5 h / 5 - 10 °C View Scheme |
(S)-1-Aminoindane
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: Pd/AlO(OH) / toluene / 6 h / 70 °C / Inert atmosphere; Schlenk technique 2: Candida antarctica lipase B; Pd/AlO(OH); potassium carbonate / toluene / 12 h / 50 °C / Resolution of racemate; Inert atmosphere; Schlenk technique; Enzymatic reaction 3: triethanolamine; sodium hydroxide / water / 6.25 h / 80 °C / Reflux 4: potassium carbonate / acetonitrile / 12 h / 30 °C / Reflux 5: isopropyl alcohol / 0.5 h / 5 - 10 °C View Scheme |
3-Phenylpropionic acid
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: polyphosphoric acid / 0.5 h / 90 °C 2: hydroxylamine hydrochloride / ethanol; water / 0.75 h / Reflux 3: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 70 °C 4: Candida antarctica lipase B; Pd/AlO(OH); potassium carbonate / toluene / 12 h / 50 °C / Resolution of racemate; Inert atmosphere; Schlenk technique; Enzymatic reaction 5: triethanolamine; sodium hydroxide / water / 6.25 h / 80 °C / Reflux 6: potassium carbonate / acetonitrile / 12 h / 30 °C / Reflux 7: isopropyl alcohol / 0.5 h / 5 - 10 °C View Scheme |
2,3-dihydro-1H-inden-1-yl-acetate
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: Candida rugosa lipase / tetrahydrofuran; aq. phosphate buffer / 24 h / 30 °C / pH 7 / Resolution of racemate; Enzymatic reaction 2: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 22 h / 0 - 20 °C / Inert atmosphere 3: triphenylphosphine; potassium hydroxide; water / tetrahydrofuran / 24 h / 20 °C 4: potassium carbonate / acetonitrile / 16 h / 60 °C 5: isopropyl alcohol / 1 h / Reflux View Scheme |
1-Indanol
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: Thermomyces lanuginosus lipase / hexane / 0.25 h / 35 °C / Inert atmosphere; Resolution of racemate; Enzymatic reaction 2: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 22 h / 0 - 20 °C / Inert atmosphere 3: triphenylphosphine; potassium hydroxide; water / tetrahydrofuran / 24 h / 20 °C 4: potassium carbonate / acetonitrile / 16 h / 60 °C 5: isopropyl alcohol / 1 h / Reflux View Scheme | |
Multi-step reaction with 5 steps 1: pseudomonas fluorescens lipase / toluene / 6 h / 30 °C / Inert atmosphere; Resolution of racemate; Enzymatic reaction 2: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 22 h / 0 - 20 °C / Inert atmosphere 3: triphenylphosphine; potassium hydroxide; water / tetrahydrofuran / 24 h / 20 °C 4: potassium carbonate / acetonitrile / 16 h / 60 °C 5: isopropyl alcohol / 1 h / Reflux View Scheme | |
Multi-step reaction with 6 steps 1: dmap / dichloromethane / 4 h / 20 °C 2: Candida rugosa lipase / tetrahydrofuran; aq. phosphate buffer / 24 h / 30 °C / pH 7 / Resolution of racemate; Enzymatic reaction 3: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 22 h / 0 - 20 °C / Inert atmosphere 4: triphenylphosphine; potassium hydroxide; water / tetrahydrofuran / 24 h / 20 °C 5: potassium carbonate / acetonitrile / 16 h / 60 °C 6: isopropyl alcohol / 1 h / Reflux View Scheme |
(S)-indanol
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 22 h / 0 - 20 °C / Inert atmosphere 2: triphenylphosphine; potassium hydroxide; water / tetrahydrofuran / 24 h / 20 °C 3: potassium carbonate / acetonitrile / 16 h / 60 °C 4: isopropyl alcohol / 1 h / Reflux View Scheme |
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triphenylphosphine; potassium hydroxide; water / tetrahydrofuran / 24 h / 20 °C 2: potassium carbonate / acetonitrile / 16 h / 60 °C 3: isopropyl alcohol / 1 h / Reflux View Scheme |
(R)-1-Aminoindane
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 16 h / 60 °C 2: isopropyl alcohol / 1 h / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: hydrogenchloride / isopropyl alcohol / 0.5 h / 5 - 20 °C / Inert atmosphere 2: sodium hydroxide / toluene / 29 h / 30 °C 3: isopropyl alcohol / 1 h / 55 - 80 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 16 h / 60 °C 2: isopropyl alcohol / 1 h / 70 - 75 °C View Scheme | |
Multi-step reaction with 3 steps 1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 15 - 20 °C / Inert atmosphere 2: triphenylsilyl radical; 2-Chlorobenzeneboronic acid / toluene / 24 h / 10 - 15 °C / Inert atmosphere 3: isopropyl alcohol / 1 h / 70 - 75 °C View Scheme |
rasagiline mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sodium hydroxide / ethyl acetate / 0.5 h / 20 °C 2: hydrogenchloride / isopropyl alcohol / 0.5 h / 5 - 20 °C / Inert atmosphere 3: sodium hydroxide / toluene / 29 h / 30 °C 4: isopropyl alcohol / 1 h / 55 - 80 °C View Scheme |
rasagiline mesylate
rasagiline
Conditions | Yield |
---|---|
With sodium hydroxide In water at 3 - 5℃; for 1h; pH=7.5 - 11; Product distribution / selectivity; | 91.6% |
With sodium hydroxide In water at 3 - 5℃; pH=11; | 91.6% |
With sodium hydroxide In water; toluene pH=~ 14; | |
With sodium hydroxide In water; toluene pH=14; |
Conditions | Yield |
---|---|
With sodium hydroxide In water; toluene at 40 - 50℃; pH=14; Product distribution / selectivity; |
Product Name: Rasagiline Mesylate (CAS NO.161735-79-1)
IUPAC Name: methanesulfonic acid; (1R)-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine
Molecular Formula: C13H17NO3S
Molecular Weight: 267.343980 g/mol
Appearance: White to Off-White Crystalline Solid
Density: 1.05 g/cm3
Boiling Point: 305.5 °C at 760 mmHg
Flash Point: 146.8 °C
Categories: APIs; Chiral; Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals; Rasagiline
Rasagiline Mesylate (CAS NO.161735-79-1) is a selective irreversible MAO-B inhibitor.
Rasagiline Mesylate , its CAS NO. is 161735-79-1, the synonyms are (r)-n-2-Propynyl-1-indanamine methanesulfonate ; (1R)-2,3-Dihydro-N-2-propyn-1-yl-1H-inden-1-amine Mesylate ; (R)-N-2-Propynyl-1-indanamine Mesylate ; Agilect ; Azilect ; TVP-101 ; Rasagiline nesylate .
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