• Name

  Anamorelin

• EINECS
• CAS No. 249921-19-5
• Article Data2
• CAS DataBase
• Density 1.214
• Solubility
• Melting Point
• Formula C₃₁H₄₂N₆O₃
• Boiling Point
• Molecular Weight 546.713
• Flash Point
• Transport Information
• Appearance
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• 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)-;
• PSA 114.77000
• LogP 3.74810

Synthetic route

339539-90-1

(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

249921-19-5

Anamorelin

Conditions

Conditions	Yield
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

5241-64-5

Boc-D-Trp-OH

249921-19-5

Anamorelin

Conditions

Conditions

Yield

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

C16H25N3O*2ClH

249921-19-5

Anamorelin

Conditions

Conditions

Yield

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

153-94-6

D-tryptophan

249921-19-5

Anamorelin

Conditions

Conditions	Yield
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

C32H43N5O4

249921-19-5

Anamorelin

Conditions

Conditions	Yield
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

(R)-2-(2-tert-Butoxycarbonylamino-2-methyl-propionylamino)-3-(1H-indol-3-yl)-propionic acid methyl ester

249921-19-5

Anamorelin

Conditions

Conditions	Yield
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

159634-94-3

(R)-2-(2-tert-Butoxycarbonylamino-2-methyl-propionylamino)-3-(1H-indol-3-yl)-propionic acid

249921-19-5

Anamorelin

Conditions

Conditions	Yield
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

14907-27-8, 5619-09-0, 7524-52-9, 26988-71-6, 41222-70-2, 67557-19-1, 109492-62-8

(R)-(+)-tryptophan methyl ester hydrochloride

249921-19-5

Anamorelin

Conditions

Conditions	Yield
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

249921-19-5

Anamorelin

Anamorelin hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In Isopropyl acetate; water Concentration; Temperature; Solvent;

249921-19-5

Anamorelin

110-17-8

(2E)-but-2-enedioic acid

RC-1291 fumarate

Conditions

Conditions	Yield
Stage #1: Anamorelin With sodium carbonate In dichloromethane Stage #2: (2E)-but-2-enedioic acid In ethyl acetate; isopropyl alcohol

Anamorelin Chemical Properties

Anamorelin Specification