Aminotadalafil

Base Information

• Chemical Name: Aminotadalafil
• CAS No.: 385769-84-6
• Molecular Formula: C₂₁H₁₈N₄O₄
• Molecular Weight: 390.398
• Hs Code.: 29339900
• UNII: FY501QO030
• DSSTox Substance ID: DTXSID50191896
• Nikkaji Number: J2.302.986C
• Wikidata: Q27278279
• NCI Thesaurus Code: C95961
• ChEMBL ID: CHEMBL1774619
• Mol file: 385769-84-6.mol

Synonyms:aminotadalafil

Chemical Property of Aminotadalafil

Chemical Property:

• Appearance/Colour: White powder
• Melting Point: 280-282°C
• Boiling Point: 678.9±65.0 °C(Predicted)
• PKA: 16.70±0.40(Predicted)
• Flash Point: 364.374oC
• PSA: 100.89000
• Density: 1.60±0.1 g/cm3(Predicted)
• LogP: 2.03130
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 390.13280507
• Heavy Atom Count: 29
• Complexity: 704

Purity/Quality:

98.0%, ^*data from raw suppliers

Amino Tadalafil ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Useful:

• Canonical SMILES: C1C2C(=O)N(CC(=O)N2C(C3=C1C4=CC=CC=C4N3)C5=CC6=C(C=C5)OCO6)N
• Isomeric SMILES: C1[C@@H]2C(=O)N(CC(=O)N2[C@@H](C3=C1C4=CC=CC=C4N3)C5=CC6=C(C=C5)OCO6)N
• Description: Amino tadalafil is an analog of tadalafil , a potent inhibitor of phosphodiesterase 5 with applications in several conditions, including erectile dysfunction, pulmonary arterial hypertension, and lower urinary tract dysfunction. Amino tadalafil has been detected as an illegal adulterant in a dietary supplement marketed for “tonic effect.”
• Uses: Amino Tadalafil is a drug analog of Tadalafil that used to treatment of male erectile dysfunction drugs.

Technology Process of Aminotadalafil

There total 5 articles about Aminotadalafil 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: 82.0%

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) → amino tadalafil (385769-84-6)

Guidance literature:

With hydrazine; In tetrahydrofuran; methanol; water; at 20 ℃; for 108h;

Reference yield: 56.0%

hydrazine hydrate (7803-57-8,79785-97-0) + 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) → amino tadalafil (385769-84-6)

Guidance literature:

In ethanol; Microwave irradiation;

DOI:10.1021/jm1014617

Reference yield:

piperonal (120-57-0,30024-74-9) → amino tadalafil (385769-84-6)

Guidance literature:

Multi-step reaction with 3 steps

1: trifluoroacetic acid / dichloromethane / 24 h / 0 - 20 °C / Molecular sieve

2: triethylamine / chloroform / -10 °C

3: ethanol / Microwave irradiation

With triethylamine; trifluoroacetic acid; In ethanol; dichloromethane; chloroform; 1: Pictet-Spengler cyclisation;

DOI:10.1021/jm1014617

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

hydrazine hydrate

D-Tryptophan methyl ester

Refernces

• 1、 -. "Chemical compounds". Page column 10. . Retrieved 2008/06/13.