Tadalafil iMpurity D

Base Information

• Chemical Name: Tadalafil iMpurity D
• CAS No.: 951661-81-7
• Molecular Formula: C₂₂H₂₀ClN₃O₄
• Molecular Weight: 425.871
• Mol file: 951661-81-7.mol

Synonyms:(1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-N-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide

Chemical Property of Tadalafil iMpurity D

Chemical Property:

• Boiling Point: 720.5±60.0 °C(Predicted)
• PKA: 14.98±0.40(Predicted)
• Density: 1.429±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

(1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-N-methyl-1H-pyrido[3,4-b]indole-3-carboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-N-methyl-1H-pyrido[3,4-b]indole-3-carboxamide is an impurity of Tadalafil (T004500), a phosphodiesterase 5 inhibitor that is used to treat erectile dysfunction.

Technology Process of Tadalafil iMpurity D

There total 2 articles about Tadalafil iMpurity D 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: 50.0%

C20H19N3O3 (951661-83-9) + chloroacetyl chloride (79-04-9) → (1S,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-N-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide + (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-N-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide (951661-81-7)

Guidance literature:

C₂₀H₁₉N₃O₃; chloroacetyl chloride; With triethylamine; In dichloromethane; at -5 - 5 ℃; for 1.5 - 2.5h;

With sodium hydrogencarbonate; In dichloromethane; water; at 5 - 30 ℃; for 0.25h; Product distribution / selectivity;

Reference yield:

(1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-N-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide (951661-82-8) + chloroacetyl chloride (79-04-9) → (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-N-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide (951661-81-7)

Guidance literature:

(1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-N-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide; chloroacetyl chloride; With triethylamine; In dichloromethane; chloroform; at -5 - 30 ℃; for 2.5h;

With sodium hydrogencarbonate; In dichloromethane; chloroform; water; at -5 - 30 ℃; Product distribution / selectivity;

Reference yield: 48.0%

(1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-N-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide (951661-81-7) → (6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione (171596-29-5)

Guidance literature:

(1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-N-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -50 - -35 ℃; for 2 - 6h;

With ammonium chloride; In tetrahydrofuran; hexane; water; ethyl acetate; at -40 - 30 ℃; Product distribution / selectivity;

upstream raw materials:

(1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-N-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide

chloroacetyl chloride

C₂₀H₁₉N₃O₃

Downstream raw materials:

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Refernces