629652-72-8

Basic information

• Product Name: ent-Tadalafil
• Synonyms: ent-Tadalafil;(S,S)-Tadalafil;(6S,12aS)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-Methyl-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione;L-Tadalafil;L-Tildenafil;Tadalafil IMpurity: IMpurity G;Tadalafil EP IMpurity B (ent-tadalafil);Pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, 6-(1,3- benzodioxol-5-yl)-2,3,6,7,12, 12a-hexahydro-2-Methyl-,(6S, 12aS)-
• CAS NO: 629652-72-8
• Molecular Formula: C22H18N3O4
• Molecular Weight: 388.39602
• Product Categories: Chiral Reagents;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 629652-72-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 278-282°C
• Boiling Point: 679.1±55.0 °C(Predicted)
• Appearance: /
• Density: 1.51±0.1 g/cm3(Predicted)
• Storage Temp.: -20?C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• PKA: 16.68±0.40(Predicted)
• CAS DataBase Reference: ent-Tadalafil(CAS DataBase Reference)
• NIST Chemistry Reference: ent-Tadalafil(629652-72-8)
• EPA Substance Registry System: ent-Tadalafil(629652-72-8)

Safety Data

• Hazardous Substances Data: 629652-72-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 629652-72-8 differently. You can refer to the following data:
1. Tadalafil (T004500) analog. Tadalafil Impurity (6S,12aS)
2. Tadalafil (T004500) analog.

Upstream product

• 74-89-5 methylamine 
• 629652-40-0 (1S,3R)-1-benzo[1,3]dioxol-5-yl-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 4299-70-1 L-tryptophan methyl ester 
• 593-51-1 methylamine hydrochloride 
• 629652-42-2 methyl (1S,3S)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 73-22-3 L-Tryptophan 
• 171596-43-3 (1S,3S)-1-(3,4-methylenedioxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester 
• 120-57-0 piperonal 
• 171596-42-2 (1S,3R)-1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahidro-9H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester 
• 14907-27-8 (R)-(+)-tryptophan methyl ester hydrochloride 

Downstream Products

• 531500-48-8 11-benzo[1,3]dioxol-5-yl-3-methyl-2,3,4a,11-tetrahydro-10H-3,10,11a-triaza-benzo[b]fluorene-1,4,5-trione 
• 171596-28-4 (6S,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12a tetrahydropyrazino [1',2':1,6] pyrido[3,4b] indole1,4(6H,7H)-dione 

Relevant articles and documents

Diastereospecific Synthesis of Tetrahydroisoquinolines via Radical Cyclization: Application in the Synthesis of ent-Tadalafil

An enantioselective synthesis of 1-substituted tetrahydroisoquinolines from L–Dopa methyl ester through intramolecular aryl radical cyclization is demonstrated. The strategy consists of bromination of (S)-2-amino-3-(2-bromo-4,5-dimethoxyphenyl)propanoate followed by condensation with various aldehydes to afford bromoimidate ester. Aryl radicals generated from bromoimidate ester under the radical generating conditions (nBu3SnH/AIBN) cyclizes via 6-endo mode to afford cis-1-substituted tetrahydroisoquinolines exclusively in 99% ee. The utility of this synthetic protocol is demonstrated in the synthesis of (6S, 12aS) Tadalafil (5 steps, 21%, 99% ee). (Figure presented.).

Synthesis and SAR of tetracyclic pyrroloquinolones as phosphodiesterase 5 inhibitors

The synthesis of the fused tetracyclic pyrroloquinolones 9a-i in four steps is described. The PDE5 inhibitory activities of these compounds, their selectivities against PDE1, PDE2, PDE3, PDE4 and PDE6, the preclinical pharmacokinetic assessments and the in vivo efficacy in increasing intracavernosal pressure are presented and discussed.

TETRACYCLIC CYCLIC GMP-SPECIFIC PHOSPHODIESTERASE INHIBITORS, PROCESS OF PREPARATION AND USE

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