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CAS No.: | 249921-19-5 |
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Name: | Anamorelin |
Article Data: | 2 |
Molecular Structure: | |
Formula: | C31H42N6O3 |
Molecular Weight: | 546.713 |
Synonyms: | 3-Piperidinecarboxylicacid, 1-(2-methylalanyl-D-tryptophyl)-3-(phenylmethyl)-, trimethylhydrazide,(3R)- (9CI);(3R)-1-(2-Methylalanyl-D-tryptophyl)-3-(phenylmethyl)-3-piperidinecarboxylic acid 1,2,2-trimethylhydrazide;RC 1291;3-Piperidinecarboxylicacid,1-[(2R)-2-[(2-amino-2-methyl-1-oxopropyl)amino]-3-(1H-indol-3-yl)-1-oxopropyl]-3-(phenylmethyl)-,1,2,2-trimethylhydrazide, (3R)-; |
Density: | 1.214 |
PSA: | 114.77000 |
LogP: | 3.74810 |
(R,R)-{1-[2-[3-benzyl-3-(N,N',N'-trimethyl-hydrazinocarbonyl)piperidin-1-yl]-1-(1H-indol-3-ylmethyl)-2-oxo-ethylcarbamoyl]-1-methylethyl}carbamic acid tert-butyl ester
Anamorelin
Conditions | Yield |
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Stage #1: (R,R)-{1-[2-[3-benzyl-3-(N,N',N'-trimethyl-hydrazinocarbonyl)piperidin-1-yl]-1-(1H-indol-3-ylmethyl)-2-oxo-ethylcarbamoyl]-1-methylethyl}carbamic acid tert-butyl ester With methanol; methanesulfonic acid at 50 - 70℃; for 0.75h; Stage #2: With potassium hydroxide In methanol; water at 22 - 70℃; for 43h; Stage #3: In water at 50℃; for 41h; Product distribution / selectivity; | 81% |
With hydrogenchloride In ethyl acetate | |
Stage #1: (R,R)-{1-[2-[3-benzyl-3-(N,N',N'-trimethyl-hydrazinocarbonyl)piperidin-1-yl]-1-(1H-indol-3-ylmethyl)-2-oxo-ethylcarbamoyl]-1-methylethyl}carbamic acid tert-butyl ester With methanesulfonic acid In methanol at 55 - 60℃; for 1h; Inert atmosphere; Stage #2: With potassium hydroxide In methanol; water at 20 - 70℃; Inert atmosphere; | 595 g |
Boc-D-Trp-OH
Anamorelin
Conditions | Yield |
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Multi-step reaction with 4 steps 1: 1-hydroxy-7-aza-benzotriazole; 4-methyl-morpholine; N,N-dimethyl acetamide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride 2: hydrogenchloride / ethyl acetate 3: 1-hydroxy-7-aza-benzotriazole; 4-methyl-morpholine; N,N-dimethyl acetamide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride 4: hydrogenchloride / ethyl acetate View Scheme |
Anamorelin
Conditions | Yield |
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Multi-step reaction with 4 steps 1: 1-hydroxy-7-aza-benzotriazole; 4-methyl-morpholine; N,N-dimethyl acetamide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride 2: hydrogenchloride / ethyl acetate 3: 1-hydroxy-7-aza-benzotriazole; 4-methyl-morpholine; N,N-dimethyl acetamide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride 4: hydrogenchloride / ethyl acetate View Scheme |
D-tryptophan
Anamorelin
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: 38 °C 2.1: 3-hydroxy-3,4-dihydrobenzotriazine-4-one; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C 2.2: 20 °C 3.1: hydrogenchloride / ethyl acetate View Scheme | |
Multi-step reaction with 3 steps 1: 38 °C 2: triethylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 h / 25 °C / Inert atmosphere 3: hydrogenchloride / ethyl acetate View Scheme |
Anamorelin
Conditions | Yield |
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Multi-step reaction with 3 steps 1: hydrogenchloride / ethyl acetate 2: 1-hydroxy-7-aza-benzotriazole; 4-methyl-morpholine; N,N-dimethyl acetamide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride 3: hydrogenchloride / ethyl acetate View Scheme |
Anamorelin
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: sodium hydroxide / water; tert-butyl methyl ether / 20 °C / Large scale 2.1: 3-hydroxy-3,4-dihydrobenzotriazine-4-one; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C 2.2: 20 °C 3.1: hydrogenchloride / ethyl acetate View Scheme | |
Multi-step reaction with 3 steps 1: sodium hydroxide / water; tert-butyl methyl ether / 20 °C / Large scale 2: triethylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 h / 25 °C / Inert atmosphere 3: hydrogenchloride / ethyl acetate View Scheme |
(R)-2-(2-tert-Butoxycarbonylamino-2-methyl-propionylamino)-3-(1H-indol-3-yl)-propionic acid
Anamorelin
Conditions | Yield |
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Multi-step reaction with 2 steps 1.1: 3-hydroxy-3,4-dihydrobenzotriazine-4-one; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C 1.2: 20 °C 2.1: hydrogenchloride / ethyl acetate View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 h / 25 °C / Inert atmosphere 2: hydrogenchloride / ethyl acetate View Scheme |
(R)-(+)-tryptophan methyl ester hydrochloride
Anamorelin
Conditions | Yield |
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Multi-step reaction with 4 steps 1.1: triethylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h / 38 °C / Inert atmosphere; Large scale 2.1: sodium hydroxide / water; tert-butyl methyl ether / 20 °C / Large scale 3.1: 3-hydroxy-3,4-dihydrobenzotriazine-4-one; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C 3.2: 20 °C 4.1: hydrogenchloride / ethyl acetate View Scheme | |
Multi-step reaction with 4 steps 1: triethylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h / 38 °C / Inert atmosphere; Large scale 2: sodium hydroxide / water; tert-butyl methyl ether / 20 °C / Large scale 3: triethylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 h / 25 °C / Inert atmosphere 4: hydrogenchloride / ethyl acetate View Scheme |
Anamorelin
Conditions | Yield |
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With hydrogenchloride In Isopropyl acetate; water Concentration; Temperature; Solvent; |
Conditions | Yield |
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Stage #1: Anamorelin With sodium carbonate In dichloromethane Stage #2: (2E)-but-2-enedioic acid In ethyl acetate; isopropyl alcohol |
Molecular Structure of Anamorelin (CAS NO.249921-19-5):
Product Name: Anamorelin
Molecular Formula: C31H42N6O3
Molecular Weight: 546.70
Density: 1.214
Anamorelin (CAS NO.249921-19-5), its Synonyms are 3-Piperidinecarboxylicacid,1-[(2R)-2-[(2-amino-2-methyl-1-oxopropyl)amino]-3-(1H-indol-3-yl)-1-oxopropyl]-3-(phenylmethyl)-,1,2,2-trimethylhydrazide, (3R)- ; 3-Piperidinecarboxylicacid, 1-(2-methylalanyl-D-tryptophyl)-3-(phenylmethyl)-, trimethylhydrazide,(3R)- (9CI) ; ;(3R)-1-(2-Methylalanyl-D-tryptophyl)-3-(phenylmethyl)-3-piperidinecarboxylic acid 1,2,2-trimethylhydrazide .