Chloropretadalafil

Base Information

• Chemical Name: Chloropretadalafil
• CAS No.: 171489-59-1
• Deprecated CAS: 1224941-84-7
• Molecular Formula: C22H19ClN2O5
• Molecular Weight: 426.856
• Hs Code.: 2934999090
• European Community (EC) Number: 689-794-3
• UNII: 1P8ITA120M
• DSSTox Substance ID: DTXSID501102383,DTXSID601347683
• Nikkaji Number: J2.568.854F
• Wikidata: Q27252711
• Mol file: 171489-59-1.mol

Synonyms:(1R,3R)-1-(1,3-benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido(3,4-b)indole-3-carboxylic acid methyl ester

Chemical Property of Chloropretadalafil

Chemical Property:

• Appearance/Colour: Pale Yellow to Pale Orange Solid
• Melting Point: 230-232 oC
• Boiling Point: 627.5±55.0 °C(Predicted)
• PKA: 16.25±0.60(Predicted)
• PSA: 80.86000
• Density: 1.445
• LogP: 3.08900
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 426.0982494
• Heavy Atom Count: 30
• Complexity: 678

Purity/Quality:

99%+ ^*data from raw suppliers

(1R,3R)-Methyl-1,2,3,4-tetrahydro-2-chloroacetyl-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate(Chloropretadalafil) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC2=C(C(N1C(=O)CCl)C3=CC4=C(C=C3)OCO4)NC5=CC=CC=C25
• Isomeric SMILES: COC(=O)[C@H]1CC2=C([C@H](N1C(=O)CCl)C3=CC4=C(C=C3)OCO4)NC5=CC=CC=C25
• Uses: An intermediate in the synthesis of Tadalafil (T004500), which is used for the treatment of erectile dysfunction. A phosphodiesterase 5 inhibitor. (1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9- tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic is used as an intermediate in the synthesis of Tadafil, which is used for the treatment of erectile dysfunction.

Technology Process of Chloropretadalafil

There total 19 articles about Chloropretadalafil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

chloroacetyl chloride (79-04-9) + (1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride (171752-68-4) → methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate (171489-59-1)

Guidance literature:

With triethylamine; In ethyl acetate; at 5 - 20 ℃; for 1.66667h; Product distribution / selectivity;

Reference yield: 95.2%

chloroacetyl chloride (79-04-9) + (1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate (171596-41-1) → methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate (171489-59-1)

Guidance literature:

(1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate; With triethylamine; In dichloromethane; at 20 ℃; for 0.166667h; Large scale;

chloroacetyl chloride; In dichloromethane; at 20 ℃; for 1h; Large scale;

Reference yield: 86.0%

piperonal (120-57-0,30024-74-9) + (R)-(+)-tryptophan methyl ester hydrochloride (14907-27-8,5619-09-0,7524-52-9,26988-71-6,41222-70-2,67557-19-1,109492-62-8) + chloroacetyl chloride (79-04-9) → methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate (171489-59-1)

Guidance literature:

piperonal; (R)-(+)-tryptophan methyl ester hydrochloride; at 85 ℃; for 3h;

chloroacetyl chloride; With triethylamine; In tetrahydrofuran; water; at 0 - 10 ℃; for 1h; Product distribution / selectivity;

upstream raw materials:

chloroacetyl chloride

(1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate

(1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride

piperonal

Downstream raw materials:

(6R,12aR)-6-benzo[1,3]dioxol-5-yl-2-[2-(4-hydroxyphenyl)ethyl]-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido-[3,4-b]indole-1,4-dione

(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-(2-(benzyl(methyl)amino)ethyl)-2,3,6,7,12,12a-hexahydropyrazino[1′,2′:1,6]pyrido-[3,4-b]indole-1,4-dione

(6R,12aR)-6-benzo[1,3]dioxol-5-yl-2-(4-morpholin-4-ylbenzyl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido-[3,4-b]indole-1,4-dione

amino tadalafil

Refernces

• 1、 Daugan, Alain,Grondin, Pascal,Ruault, Cécile,Le Monnier de Gouville, Anne-Charlotte,Coste, Hervé,Linget, Jean Michel,Kirilovsky, Jorge,Hyafil, Fran?ois,Labaudinièret, Richard. "The discovery of tadalafil: A novel and highly selective PDE5 inhibitor. 2: 2,3,6,7,12,12a-Hexahydropyrazino[1′,2′ :1,6]pyrido[3,4-b]indole-1,4-dione analogues". . p. 4533 - 4542. Retrieved 2003.
• 2、 Xiao, Sen,Shi, Xiao-Xin,Xing, Jing,Yan, Jing-Jing,Liu, Shi-Ling,Lu, Wei-Dong. "Synthesis of tadalafil (Cialis) from l-tryptophan". . p. 2090 - 2096. Retrieved 2009.
• 3、 Shi, Xiao-Xin,Liu, Shi-Ling,Xu, Wei,Xu, Yu-Lan. "Highly stereoselective Pictet-Spengler reaction of d-tryptophan methyl ester with piperonal: convenient syntheses of Cialis (Tadalafil), 12a-epi-Cialis, and their deuterated analogues". . p. 435 - 442. Retrieved 2008.
• 4、 -. "Preparation method of phosphodiesterase inhibitor". Paragraph 0016; 0041-0055. . Retrieved 2021/11/03.
• 5、 -. "Production process of tadalafil bulk drug". Paragraph 0014; 0017. . Retrieved 2020/07/02.