Tadalafil Impurity 19

Base Information

• Chemical Name: Tadalafil Impurity 19
• CAS No.: 477970-21-1
• Molecular Formula: C₂₃H₂₁N₃O₄
• Molecular Weight: 403.437
• DSSTox Substance ID: DTXSID401105172
• ChEMBL ID: CHEMBL2011387
• Mol file: 477970-21-1.mol

Synonyms:477970-21-1;Tadalafil Impurity 19;SCHEMBL4701524;CHEMBL2011387;DTXSID401105172;EX-A3373;(2R,8R)-2-(1,3-Benzodioxol-5-yl)-6,17-dimethyl-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-4,7-dione;(6R,12aR)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2,7-dimethylpyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Chemical Property of Tadalafil Impurity 19

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 403.15320616
• Heavy Atom Count: 30
• Complexity: 731

Purity/Quality:

>95% ^*data from raw suppliers

N-methyl-Tadalafil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1CC(=O)N2C(C1=O)CC3=C(C2C4=CC5=C(C=C4)OCO5)N(C6=CC=CC=C36)C
• Isomeric SMILES: CN1CC(=O)N2[C@@H](C1=O)CC3=C([C@H]2C4=CC5=C(C=C4)OCO5)N(C6=CC=CC=C36)C
• Uses: N-methyl-Tadalafil is an impurity of Tadalafil (T004500), which is used for the treatment of erectile dysfunction. A phosphodiesterase 5, and TbrPDEB1 inhibitor.

Technology Process of Tadalafil Impurity 19

There total 2 articles about Tadalafil Impurity 19 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:

(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) + methyl iodide (74-88-4) → (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,7-dimethyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione (477970-21-1)

Guidance literature:

(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; With sodium hydride; In tetrahydrofuran; mineral oil; at 20 ℃; for 0.583333h;

methyl iodide; In tetrahydrofuran; mineral oil; for 3h;

DOI:10.1016/j.bmcl.2012.01.118

Reference yield:

methyl 1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate (1321600-91-2) → (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,7-dimethyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione (477970-21-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / methanol / Reflux

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.58 h / 20 °C

2.2: 3 h

With sodium hydride; triethylamine; In tetrahydrofuran; methanol; mineral oil;

DOI:10.1016/j.bmcl.2012.01.118

upstream raw materials:

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

(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

methyl iodide

Refernces