171596-41-1

Basic information

• Product Name: (1R,3R)-METHYL-1,2,3,4-TETRAHYDRO-1-(3,4-METHYLENEDIOXYPHENYL)-9H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLATE
• Synonyms: (1R,3R)-METHYL-1,2,3,4-TETRAHYDRO-1-(3,4-METHYLENEDIOXYPHENYL)-9H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLATE;1H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLIC ACID, 1-(1,3-BENZODIOXOL-5-YL)-2,3,4,9-TETRAHYDRO-, METHYL ESTER, (1R,3R)-;1H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLICACID, 1-(1,3-BENZODIOXOL-5-YL)-2,3,4,9-TETRAHYDRO-METHYLESTER,(1R,3R)-;(1R,3R)-1-(1,3-Benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester;(1R,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-Methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate HYDROCHLORIDE;(1R,3R)-Methyl 1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate;Tadalafil IntermediateⅢ;(1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-3-carboxylic acid methyl ester
• CAS NO: 171596-41-1
• Molecular Formula: C₂₀H₁₈N₂O₄
• Molecular Weight: 350.37
• EINECS: 1312995-182-4
• Product Categories: Chiral Reagents
• Mol File: 171596-41-1.mol
• Article Data: 33

Chemical Properties

• Melting Point: 83-85°C
• Boiling Point: 530.977°C at 760 mmHg
• Flash Point: 274.925°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.664
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 16.87±0.60(Predicted)
• CAS DataBase Reference: (1R,3R)-METHYL-1,2,3,4-TETRAHYDRO-1-(3,4-METHYLENEDIOXYPHENYL)-9H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3R)-METHYL-1,2,3,4-TETRAHYDRO-1-(3,4-METHYLENEDIOXYPHENYL)-9H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLATE(171596-41-1)
• EPA Substance Registry System: (1R,3R)-METHYL-1,2,3,4-TETRAHYDRO-1-(3,4-METHYLENEDIOXYPHENYL)-9H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLATE(171596-41-1)

Safety Data

• Hazardous Substances Data: 171596-41-1(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Powder

Uses

Different sources of media describe the Uses of 171596-41-1 differently. You can refer to the following data:
1. (1R,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-Methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate can be used as an intermediate in the synthesis of Tadafil, which is used for the treatment of erectile dysfunction.
2. An intermediate and impurity in the synthesis of Tadafil.
3. An intermediate and impurity in the synthesis of Tadalafil (T004500).

InChI:InChI=1/C20H18N2O4/c1-24-20(23)15-9-13-12-4-2-3-5-14(12)21-19(13)18(22-15)11-6-7-16-17(8-11)26-10-25-16/h2-8,15,18,21-22H,9-10H2,1H3/t15-,18-/m1/s1

Upstream product

• 120-57-0 piperonal 
• 153-94-6 D-tryptophan 
• 495-76-1 piperonol 
• 4299-70-1 L-tryptophan methyl ester 
• 1039484-71-3 (3R)-1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahidro-9H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester 
• 67-56-1 methanol 
• 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 
• 474668-76-3 (1R,3R)-1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid hydrochloride 
• 14907-27-8 (R)-(+)-tryptophan methyl ester hydrochloride 
• 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 
• 4299-70-1 D-Tryptophan methyl ester 
• 749864-17-3 (R)-2-{[1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester 
• 17680-04-5 (3,4-methylenedioxy)phenylmagnesium bromide 

Downstream Products

• 171489-59-1 methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate 
• 1018814-83-9 (6R,12aR)-6-benzo[1,3]dioxol-5-yl-2-((R)-1-(4-dimethylaminobenzyl)pyrrolidin-3-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione 

Relevant articles and documents

One-pot pictet-spengler reaction and esterification for the preparation of a key tadalafil synthetic intermediate

A new method is reported for the preparation of 2,3,4,9-tetrahydro-1H- β-carboline-3-carboxylic acid methyl ester, a key intermediate in the synthesis of Tadalafil which is used for the treatment of male erectile dysfunction, via one-pot esterification and Pictet-Spengler reaction.

Production process of tadalafil bulk drug

The invention belongs to the technical field of medicines, and particularly relates to a production process of a tadalafil bulk drug. The production process of the tadalafil bulk drug comprises the following steps: A1, carrying out an esterification reaction on methanol and D-tryptophan to obtain an intermediate I; A2, performing a condensation reaction on the intermediate I and heliotropin to obtain an intermediate II; A3, performing an acylation reaction on the intermediate II and chloroacetyl chloride to obtain an intermediate III; and A4, carrying out a cyclization reaction on the intermediate III and monomethylamine to obtain the tadalafil bulk drug. According to the method, a reaction path is reasonably selected, and meanwhile, the process details of each reaction step are deeply optimized, so high purity and yield of a product of each step of reaction can be obtained, the prepared tadalafil bulk drug is low in cost and good in stability, the economical efficiency of the whole reaction path is improved, and production cost is reduced.

Discovery of in Vivo Chemical Probes for Treating Alzheimer's Disease: Dual Phosphodiesterase 5 (PDE5) and Class i Histone Deacetylase Selective Inhibitors

In order to determine the contributions of histone deacetylase (HDAC) isoforms to the beneficial effects of dual phosphodiesterase 5 (PDE5) and pan-HDAC inhibitors on in vivo models of Alzheimer's disease (AD), we have designed, synthesized, and tested novel chemical probes with the desired target compound profile of PDE5 and class I HDAC selective inhibitors. Compared to previous hydroxamate-based series, these molecules exhibit longer residence times on HDACs. In this scenario, shorter or longer preincubation times may have a significant impact on the IC50 values of these compounds and therefore on their corresponding selectivity profiles on the different HDAC isoforms. On the other hand, different chemical series have been explored and, as expected, some pairwise comparisons show a clear impact of the scaffold on biological responses (e.g., 35a vs 40a). The lead identification process led to compound 29a, which shows an adequate ADME-Tox profile and in vivo target engagement (histone acetylation and cAMP/cGMP response element-binding (CREB) phosphorylation) in the central nervous system (CNS), suggesting that this compound represents an optimized chemical probe; thus, 29a has been assayed in a mouse model of AD (Tg2576).