171489-03-5

Basic information

• Product Name: (6R,trans)-6-(3,4-dihydroxyphenyl)-2,3,6,7,12,12a-hexahydro-2-Methyl-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
• Synonyms: (6R,12aR)-6-(3,4-dihydroxyphenyl)-2,3,6,7,12,12a-hexahydro-2-Methyl-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione;(6R,trans)-6-(3,4-dihydroxyphenyl)-2,3,6,7,12,12a-hexahydro-2-Methyl-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione;DesMethylene Tadalafil;Tadalafil IMpurity: IMpurity I;Tadalafil IMpurity K;Tadalafil Desmethylene Impurity;Tadalafil Catechol;(6R,12aR)-6-(3,4-Dihydroxyphenyl)-2-methyl-2,3,6,7,12,12a-hexahydro pyrazino [1′,2′:1,6]-pyrido[3,4-b]indole-1,4-dione
• CAS NO: 171489-03-5
• Molecular Formula: C21H19N3O4
• Molecular Weight: 377.39326
• Product Categories: Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 171489-03-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 735.3±60.0 °C(Predicted)
• Appearance: /
• Density: 1.56±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• PKA: 9.58±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: (6R,trans)-6-(3,4-dihydroxyphenyl)-2,3,6,7,12,12a-hexahydro-2-Methyl-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (6R,trans)-6-(3,4-dihydroxyphenyl)-2,3,6,7,12,12a-hexahydro-2-Methyl-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione(171489-03-5)
• EPA Substance Registry System: (6R,trans)-6-(3,4-dihydroxyphenyl)-2,3,6,7,12,12a-hexahydro-2-Methyl-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione(171489-03-5)

Safety Data

• Hazardous Substances Data: 171489-03-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Pale Pink Solid

Uses

Tadalafil. A phosphodiesterase 5 inhibitor.

Upstream product

• 74-89-5 methylamine 
• 14907-27-8 (R)-(+)-tryptophan methyl ester hydrochloride 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 185750-07-6 C₁₄H₁₅ClN₂O₃ 

Relevant articles and documents

Preparation method of Tadalafil compounds

The invention discloses a preparation method of Tadalafil compounds. In the synthetic method, the compound IV is obtained by two-step acylation reaction of a starting material D-tryptophan methyl ester hydrochloride with chloroacetyl chloride and 3,4-dyhydroxy-benzoyl chloride, the compound is obtained by cyclization reaction of the compound IV with phosphorus acyl halide, the compound VI is generated from the compound V via asymmetric hydride reaction and is then reacted with methylamine, and the final Tadalafil compounds are obtained through cyclization reaction of dibromomethane. With the method, use of heliotropin of state controlled chemicals is avoided, cis-type carbine intermediate is obtained by adopting asymmetric hydrogenation, and ee value is above 99%; the preparation method is simple in operation and synthetic reaction, moderate in reaction condition, high in purity and yield, and suitable for industrialized production.

Key intermediate and synthesis method thereof, and application of key intermediate in preparing tadalafil

The invention discloses a key intermediate and a synthesis method thereof, and application of the key intermediate in preparing tadalafil. The synthesis method comprises the following steps: by using D-tryptophan methyl ester hydrochloride and 3,4-dihydroxybenzaldehyde as raw materials, carrying out condensation cyclization, chloracetylation and aminolysis cyclization to generate the key intermediate for preparing tadalafil. The method has the advantage of accessible raw materials, and overcomes the technical defects due to the use of the police-controlled precursor chemical heliotropin as the raw material in the prior art. The method has the advantages of no need of any catalyst and high yield in the preparation process. The obtained key intermediate can be used for preparing tadalafil. Thus, the synthesis method is simple and easy to implement, has the advantages of stable technique and low cost, and is suitable for industrial large-scale production. The structural formula of the key intermediate is disclosed as Formula (III).