406938-39-4

Basic information

• Product Name: (1R,3R)-1-(1,3-benzodioxol-5-yl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid
• CAS NO: 406938-39-4
• Molecular Weight: 336.347
• Mol File: 406938-39-4.mol

Chemical Properties

• Boiling Point: 595.6±50.0 °C(Predicted)
• Density: 1.447±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (1R,3R)-1-(1,3-benzodioxol-5-yl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3R)-1-(1,3-benzodioxol-5-yl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid(406938-39-4)
• EPA Substance Registry System: (1R,3R)-1-(1,3-benzodioxol-5-yl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid(406938-39-4)

Safety Data

• Hazardous Substances Data: 406938-39-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Elzivirine is utilized as an anti-HIV drug, functioning as a non-nucleoside reverse transcriptase inhibitor. Its distinctive structure and pharmacological properties make it a promising candidate for further research and development in the fight against HIV/AIDS. It offers a novel approach to inhibiting the replication of the virus, which could lead to more effective treatment options for patients.

Upstream product

• 171596-41-1 (1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate 
• 120-57-0 piperonal 
• 153-94-6 D-tryptophan 
• 59259-90-4 5-(dimethoxymethyl)benzo[d][1,3]dioxole 
• 171752-68-4 (1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride 

Downstream Products

• 2058231-15-3 (1R,3R)-1-(1,3-benzodioxol-5-yl)-2-(2-methylaminoacetyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid 

Relevant articles and documents

Alternative synthesis of tadalafil: PDE5 inhibitor

Two-step alternative synthesis of tadalafil (1) is described. The synthesis features Pictet-Spengeler type reaction and DCC (N,N′- dicyclohexylcarbodiimide)/HOBt (N-hydroxybenzotriazole)-mediated double amidation employing sarcosine ethyl ester hydrochlor

Preparation method of tadalafil intermediate

The invention discloses a preparation method of a tadalafil intermediate, which comprises: S1, carrying out a reaction on piperonyl alcohol, oxygen and a catalyst in an organic solvent, washing with ahydrochloric acid aqueous solution, and removing the aqueous phase by layering to obtain a piperonal solution; s2, adding D-tryptophan and trifluoroacetic acid into the piperonal solution, reacting in an inert gas atmosphere, then washing with an alkaline aqueous solution, and removing an aqueous phase by layering to obtain an intermediate solution; s3, taking the intermediate solution, evaporating to remove the organic solvent, adding an inorganic acid and water, continuously reacting in an inert gas atmosphere, and purifying to obtain the tadalafil intermediate. According to the method, thepiperonyl alcohol is used as a starting material, so that the use of a controlled easily-prepared drug piperonal raw material is avoided; no organic solvent is needed in the configuration conversionprocess, a single-configuration product is directly obtained, reaction conditions of all steps are mild, operation is easy, the method is suitable for industrial production, and the prepared tadalafilintermediate is good in purity and low in isomer content.

Method for synthesizing tadalafil

The invention discloses a method for synthesizing tadalafil. Tadalafil is synthesized from D-tryptophan and a compound of formula 1. The method for preparing tadalafil of the invention can effectivelyprepare tadalafil. In addition, the starting material piperonyl dimethyl acetal of the preparation method is easy to obtain as a non-controlled material, the procurement and management are not restricted, the use of the controlled material piperonyl is effectively avoided, the management and procurement are convenient, the process steps are short, the production cost is greatly reduced, and the preparation method is more suitable for large-scale and industrial production of tadalafil.

Impurity reference substance of tadalafil and preparation method of impurity reference substance

The invention relates to an impurity reference substance of tadalafil and a preparation method of the impurity reference substance. The invention discloses compounds represented by formulae I and II shown in the description, wherein R1 is selected from halogen or NR2R3; and R2 and R2 are respectively independently selected from H or C1-C4 alkyl. The invention further discloses a preparation method of the compounds. Compounds M2Z1, M2Z2, Z1 and Z2 have high purities and can be used as reference substances for detecting or monitoring the impurity content and the product quality of non-bulk drugs and intermediates of tadalafil, so that the medication safety of tadalafil is guaranteed; furthermore, the preparation method of the impurity reference substance is simple and convenient, the operation and the control are simple, the energy consumption is low, the consumed time is short, the production efficiency is high, the cost is low, and the economic value is obvious; and the impurity reference substance has a very good industrial prospect.

Chemical compounds

Compounds of the general structural formula and use of the compounds and salts and solvates thereof, as therapeutic agents.