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Anamorelin

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Name

Anamorelin

EINECS N/A
CAS No. 249921-19-5 Density 1.214
PSA 114.77000 LogP 3.74810
Solubility N/A Melting Point N/A
Formula C31H42N6O3 Boiling Point N/A
Molecular Weight 546.713 Flash Point N/A
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 249921-19-5 (Anamorelin) Hazard Symbols N/A
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)-;

Article Data 2

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

Anamorelin Chemical Properties

Molecular Structure of Anamorelin (CAS NO.249921-19-5):

Product Name: Anamorelin 
Molecular Formula: C31H42N6O3
Molecular Weight: 546.70 
Density: 1.214

Anamorelin Specification

  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 .

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