55375-92-3

Basic information

• Product Name: (R)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one
• Synonyms: (R)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one;D-Praziquanamine;(R)-praziquanamine
• CAS NO: 55375-92-3
• Molecular Formula: C₁₂H₁₄N₂O
• Molecular Weight: 202.25236
• Mol File: 55375-92-3.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• Solubility: Chloroform; Dichloromethane
• CAS DataBase Reference: (R)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one(55375-92-3)
• EPA Substance Registry System: (R)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one(55375-92-3)

Safety Data

• Hazardous Substances Data: 55375-92-3(Hazardous Substances Data)

Usage

Description

(R)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one is a complex organic compound with a unique molecular structure. It is characterized by its tetrahydro-pyrazino-isoquinolinone core, which is derived from the fusion of a pyrazine and isoquinoline ring systems. (R)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one has potential applications in various fields due to its distinct chemical properties and structural features.

Uses

Used in Pharmaceutical Industry:
(R)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one is used as an intermediate in the synthesis of (R)-Praziquantel-d11 (P702102), an important compound with demonstrated antiparasitic activity. (R)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one is particularly effective against juvenile Schistosoma mansoni infestations in mice, exhibiting both in vitro and in vivo inhibition of the parasite. The development of (R)-Praziquantel-d11 as a pharmaceutical agent could lead to new treatments for parasitic infections, offering a valuable contribution to global health.
Used in Chemical Synthesis:
Due to its unique structure, (R)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one may also find use in the chemical synthesis industry. It could serve as a key building block or precursor for the development of novel compounds with various applications, such as pharmaceuticals, agrochemicals, or materials science. (R)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one's structural diversity and potential for functionalization make it an attractive candidate for further research and development in these fields.

Upstream product

• 210223-97-5 2-[(2,2-dimethoxyethyl)amino]-N-(2-phenylethyl)acetamide hydrochloride 
• 64-04-0 phenethylamine 
• 13156-95-1 2-chloro-N-phenethylacetamide 
• 1622136-46-2 (R)-praziquanamine-hemi-dibenzoyl-L-tataric acid salt 
• 99746-73-3 (S)-(-)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 
• 55375-96-7 C₁₇H₁₈N₂O 
• 106181-28-6 ethyl (+/-)-1,2,3,4-tetrahydroisoquinoline-1-carboxylate 
• 32909-74-3 1-methoxycarbonyl-1,2,3,4-tetrahydroisoquinoline 
• 1622136-46-2 (R)-praziquanamine dibenzoyl-L-tartaric acid salt 
• 61196-37-0 2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one 

Downstream Products

• 99780-88-8 (-)-1,3,4,6,7,11b-Hexahydro-2H-pyrazino<2,1-a>isochinolin 
• 99780-87-7 (+)-1,3,4,6,7,11b-Hexahydro-2H-pyrazino<2,1-a>isochinolin 
• 135526-78-2 (-)-Praziquantel 
• 1558003-78-3 (R)-(-)-2-(cis-4-(benzyloxy)cyclohexanecarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 
• 134924-69-9 (-)-2-(4-cis-hydroxycyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one 
• 1558003-79-4 (R)-(-)-2-(trans-4-(benzyloxy)cyclohexanecarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 
• 1609986-44-8 C₁₉H₁₉N₃O₂ 
• 1609979-49-8 C₂₈H₂₂F₃N₅O₃ 
• 1609979-50-1 C₃₁H₂₄F₃N₅O₃ 
• 1609986-43-7 C₁₉H₁₇N₃O₄ 
• 1609979-51-2 C₂₃H₂₃N₃O₂ 
• 1609979-52-3 C₃₄H₄₀N₆O₄ 
• 1399880-38-6 (R)-2-(cyclohexane-d11-carbonyl)-2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one 
• 134924-73-5 (-)-2-(4-trans-hydroxycyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one 

Relevant articles and documents

Combining Incompatible Processes for Deracemization of a Praziquantel Derivative under Flow Conditions

An efficient deracemization method for conversion of the racemate to the desirable (R)-enantiomer of Praziquantel has been developed by coupling incompatible racemization and crystallization processes. By a library approach, a derivative that crystallizes as a conglomerate has been identified. Racemization occurs via reversible hydrogenation over a palladium on carbon (Pd/C) packed column at 130 °C, whereas deracemization is achieved by alternating crystal growth/dissolution steps with temperature cycling between 5–15 °C. These incompatible processes are combined by means of a flow system resulting in complete deracemization of the solid phase to the desired (R)-enantiomer (98 % ee). Such an unprecedented deracemization by a decoupled crystallization/racemization approach can readily be turned into a practical process and opens new opportunities for the development of essential enantiomerically pure building blocks that require harsh methods for racemization.

One-pot palladium-catalyzed racemization of (S)-praziquanamine: A key intermediate for the anthelmintic agent (R)-praziquantel

An one-pot palladium-catalyzed procedure for racemization of (S)-praziquanamine, which is the undesired enantiomer and produced during the resolution step for preparing the anthelmintic drug (R)-praziquantel, has been developed through dehydrogenation of

METHOD FOR THE PRODUCTION OF PRAZIQUANTEL AND PRECURSORS THEREOF

The present invention relates to methods for the production of enantiopure or enantioenriched Praziquantel precursors and to methods for the production of enantiopure or enantioenriched Praziquantel comprising the methods for the production of the Praziquantel precursors. The present invention further relates to compounds or intermediates useful in such methods.