Nortadalafil

Base Information

• Chemical Name: Nortadalafil
• CAS No.: 171596-36-4
• Molecular Formula: C21H17N3O4
• Molecular Weight: 375.384
• UNII: 5W59DMB3LD
• DSSTox Substance ID: DTXSID40431339
• Nikkaji Number: J3.513.666E
• Wikidata: Q27262952
• ChEMBL ID: CHEMBL342008
• Mol file: 171596-36-4.mol

Synonyms:Nortadalafil;171596-36-4;Demethyltadalafil;Demethyl Tadalafil;(+)-Nortadalafil;5W59DMB3LD;CHEMBL342008;N-Desmethyl Tadalafil;(2R,8R)-2-(1,3-benzodioxol-5-yl)-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-4,7-dione;Desmethyltadalafil (Nortadalafil);(6R,12aR)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione;(6R,12aR)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione;629652-62-6;Pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-, (6R,12aR)-;Pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-, (6R-trans)-;Tadalafil-Nor;Desmethyl Tadalafil;Pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-, (6R,12aR)-;Pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-, (6R-trans)-;UNII-5W59DMB3LD;SCHEMBL1326910;DTXSID40431339;GLXC-27041;BDBM50134133;MFCD19443817;AKOS027250761;CS-0823;AS-56845;HY-90009;J3.513.666E;C90282;A899415;EN300-20385208;Q27262952;Z3244741608;(2R,8R)-2-(1,3-dioxaindan-5-yl)-3,6,17-triazatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1(10),11(16),12,14-tetraene-4,7-dione;(2R,8R)-2-(2H-1,3-benzodioxol-5-yl)-3,6,17-triazatetracyclo[8.7.0.0?,?.0??,??]heptadeca-1(10),11(16),12,14-tetraene-4,7-dione;(5R,6R)-6-Benzo[1,3]dioxol-5-yl-2,3,6,7,12,12a-hexahydro-pyrazino[1'',2'':1,6]pyrido[3,4-b]indole-1,4-dione;(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione;Pyrazino[1 inverted exclamation marka,2 inverted exclamation marka:1,6]pyrido[3,4-b]indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-, (6R,12aR)-rel-

Chemical Property of Nortadalafil

Chemical Property:

• Appearance/Colour: yellow powder
• Melting Point: 285-290 oC (methanol )
• Boiling Point: 718.6±60.0 °C(Predicted)
• PKA: 13.53±0.40(Predicted)
• PSA: 87.15000
• Density: 1.55±0.1 g/cm3 (20 oC 760 Torr)
• LogP: 2.08290
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 375.12190603
• Heavy Atom Count: 28
• Complexity: 672

Purity/Quality:

97% ^*data from raw suppliers

N-DesmethylTadalafil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(=O)NCC(=O)N2C(C3=C1C4=CC=CC=C4N3)C5=CC6=C(C=C5)OCO6
• Isomeric SMILES: C1[C@@H]2C(=O)NCC(=O)N2[C@@H](C3=C1C4=CC=CC=C4N3)C5=CC6=C(C=C5)OCO6
• Uses: A N-desmethyl analogue of the human PDE5 inhibitor Tadalafil (T004500). A potential antiplasmodial drug.

Technology Process of Nortadalafil

There total 9 articles about Nortadalafil 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: 70.0%

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) → (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione (171596-36-4)

Guidance literature:

With ammonia; In methanol; at 45 ℃; for 20h;

DOI:10.1016/j.bmcl.2006.10.069

Reference yield:

(1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate (171596-41-1) → (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione (171596-36-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / triethylamine / CHCl₃ / -10 °C

2: 70 percent / NH₃ / methanol / 20 h / 45 °C

With ammonia; triethylamine; In methanol; chloroform;

DOI:10.1016/j.bmcl.2006.10.069

Reference yield:

D-Tryptophan methyl ester (4299-70-1,7303-49-3,22032-65-1) → (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione (171596-36-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 42 percent / TFA / CH₂Cl₂ / 20 °C

2: 93 percent / NaHCO₃ / CHCl₃ / 20 °C

3: 31 percent / methanolic NH₃ / Heating

With ammonia; sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane; chloroform; 1: Pictet-Spengler reaction;

DOI:10.1021/jm0300577

upstream raw materials:

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

piperonal

(R)-(+)-tryptophan methyl ester hydrochloride

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