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.

Compound acyl intermediate as well as synthetic method thereof and application thereof in preparing tadalafil

The invention discloses a compound acyl intermediate as well as a synthetic method and application thereof in preparing tadalafil. The synthetic method comprises the following steps: preparing (1R, 3R)-methyl-1-(3,4-dihydroxyphenyl)-2,3,4,9-tetrahydro-1H-pyridino[3,4-b]indol-3-carboxylic acid (compound I) by taking D-tryptophan methyl ester hydrochloride and 3,4-dihydroxy benzaldehyde as raw materials, and allowing the compound I to have chloroacetylation with chloroacetyl chloride to generate the compound acyl intermediate. By adopting the method, raw materials are easy to get, so that the technical weakness caused by using the poisonable chemical heliotropin controlled by the public security department in the prior art as a raw material is overcome. The preparation process requires no catalyst, and the yield is high. The obtained compound acyl intermediate can be used for preparing the tadalafil, and is simple and easy, stable in process, low in cost, and suitable for industrialized mass production. The structural formula of the compound acyl intermediate is shown as formula (II): (see the description) (II).