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CAS No.: | 239463-85-5 |
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Name: | 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate |
Article Data: | 8 |
Molecular Structure: | |
Formula: | C22H25N3O2.C4H6O6 |
Molecular Weight: | 513.547 |
Synonyms: | 3-{5[(2R)-2-aminoprppyl]-7-cyano-2,3-dihydro-1H-indol-1-yl}propyl benzoate monotartaric acid salt; (R)-5-(2-aminopropyl)-1-(3-benzoyloxypropyl) Indoline-7-Carbonitrile Tartaric acid; 5-[(2R)-2-AMINOPROPYL]-1-[3-(BENZOYLOXY)PROPYL]-2,3-DIHYDRO-1H-INDOLE-7-CARBONITRILE (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE; (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate; 3-(5-((R)-2-aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate L-tartrate; 1-(3-benzoyloxypropyl)-7-cyano-5-(2-aminopropyl)-2,3-dihydroindole; 查看更多英文别名 收起 |
EINECS: | 688-292-1 |
PSA: | 194.41000 |
LogP: | 1.70028 |
L-Tartaric acid
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
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Stage #1: C38H39N3O4 With palladium on activated charcoal; hydrogen Stage #2: L-Tartaric acid Inert atmosphere; | 33.3% |
L-Tartaric acid
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Stage #1: C42H41N3O4 With palladium on activated charcoal; hydrogen Stage #2: L-Tartaric acid Inert atmosphere; | 30.9% |
L-Tartaric acid
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
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Stage #1: 3-(5-(2-((tert-butoxycarbonyl)amino)propyl)-7-cyanoindolin-1-yl)propylbenzoate With hydrogenchloride In chloroform; water at 25 - 30℃; for 5h; Stage #2: L-Tartaric acid In water; acetone at 20 - 25℃; for 12h; | 23.5% |
L-Tartaric acid
5-(2-aminopropyl)-1-[3-(benzoyloxy)propyl]-2,3-dihydro-7-cyano-1H-indole
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
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In tetrahydrofuran; water at 20 - 65℃; Product distribution / selectivity; | |
In water; acetone at 20℃; for 49h; | 2.05 g |
1-(3-benzoyloxypropyl)-7-cyano-5-(2-nitropropyl)-2,3-dihydroindole
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
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Multi-step reaction with 2 steps 1: hydrogenchloride; zinc / water; methanol / 20 h / 60 - 65 °C 2: water; tetrahydrofuran / 20 - 65 °C View Scheme | |
Multi-step reaction with 2 steps 1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C 2: water; acetone / 49 h / 20 °C View Scheme |
1-(3-benzoyloxypropyl)-5-(2-nitro-1-propenyl)-2,3-dihydroindole
A
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
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Multi-step reaction with 5 steps 1.1: sodium tetrahydroborate; potassium hydroxide / tetrahydrofuran; water / -10 - 20 °C 2.1: trichlorophosphate / 0 - 50 °C 2.2: Cooling with ice 3.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 2 h / 50 °C 3.2: 2 h / 80 °C 4.1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave 5.1: acetone; water / 25 - 65 °C / Resolution of racemate View Scheme |
1-(3-benzoyloxypropyl)-5-(2-nitropropyl)-2,3-dihydroindole
A
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: trichlorophosphate / 0 - 50 °C 1.2: Cooling with ice 2.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 2 h / 50 °C 2.2: 2 h / 80 °C 3.1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave 4.1: acetone; water / 25 - 65 °C / Resolution of racemate View Scheme |
1-(3-benzoyloxypropyl)-7-formyl-5-(2-nitropropyl)-2,3-dihydroindole
A
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 2 h / 50 °C 1.2: 2 h / 80 °C 2.1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave 3.1: acetone; water / 25 - 65 °C / Resolution of racemate View Scheme |
1-(3-benzoyloxypropyl)-7-cyano-5-(2-nitropropyl)-2,3-dihydroindole
A
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave 2: acetone; water / 25 - 65 °C / Resolution of racemate View Scheme |
L-Tartaric acid
5-(2-aminopropyl)-1-[3-(benzoyloxy)propyl]-2,3-dihydro-7-cyano-1H-indole
A
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
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In water; acetone at 25 - 65℃; Resolution of racemate; | A n/a B n/a |