N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine; phosphoric acid

Base Information

• Chemical Name: N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine; phosphoric acid
• CAS No.: 63-45-6
• Molecular Formula: C15H21N3O^.2(H3PO4)
• Molecular Weight: 455.342
• Hs Code.: 29334900
• NSC Number: 757290,619961,149765
• ChEMBL ID: CHEMBL994
• Mol file: 63-45-6.mol

Synonyms:N4-(6-Methoxyquinolin-8-yl)pentane-1,4-diamine phosphate;N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine;phosphoric acid;NSC149765;primaquinbis(phosphat);2299-91-4;MLS001334045;4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine;Quinoline, 8-[(4-amino-1-methylbutyl)amino]-6-methoxy-, phosphate;SMR000875314;C15-H21-N3-O.2H3-O4-P;NSC619961;1,4-Pentanediamine, N4-(6-methoxy-8-quinolinyl)-, phosphate(1:2);1,4-Pentanediamine, N(4)-(6-methoxy-8-quinolinyl)-, phosphate (1:2);CHEMBL994;MLS002153831;HMS2234H13;HMS3259B03;Pharmakon1600-01500500;NSC757290;AKOS024462450;NC00607;NSC-619961;NSC-757290;66616-84-0;FT-0603262;EN300-51911;1, N4-(6-methoxy-8-quinolinyl)-, phosphate (1:2);Z732242096;N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine

Chemical Property of N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine; phosphoric acid

Chemical Property:

• Appearance/Colour: orange powder
• Vapor Pressure: 2.5E-08mmHg at 25°C
• Melting Point: 199-205 °C
• Boiling Point: 451.1 °C at 760 mmHg
• Flash Point: 226.6 °C
• PSA: 235.31000
• LogP: 1.69880
• Storage Temp.: Refrigerator
• Solubility.: water: soluble50mg/mL, clear, orange to red
• Water Solubility.: moderately soluble
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 357.14535787
• Heavy Atom Count: 24
• Complexity: 312

Purity/Quality:

99% ^*data from raw suppliers

Primaquine diphosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CCCN)NC1=C2C(=CC(=C1)OC)C=CC=N2.OP(=O)(O)O
• Uses: Antimalarial. acetylcholinesterase inhibitor Primaquine diphosphate is an established antimalarial drug used in the treatment of persistent liver forms of P. vivax or P. ovale infection for its ability to kill late-stage gametocytes and hypnozoites. In historical terms, this aminoquinoline was the stimulus for the discovery of glucose-6-phosphate (G6P) dehydrogenase deficiency as it induced hemolytic anemia in patients lacking the G6P-metabolizing enzyme.
• Clinical Use: Treatment of malaria (Plasmodium vivax and Plasmodium ovale), in combination with chloroquine Treatment of Pneumocystis jiroveci pneumonia (PCP), in combination with clindamycin
• Drug interactions: Potentially hazardous interactions with other drugs Antimalarials: avoid concomitant use with artemether/lumefantrine.

Technology Process of N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine; phosphoric acid

There total 7 articles about N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine; phosphoric acid 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:

Primaquine (90-34-6,57152-58-6) + N-phthalolylprimaquine (83532-78-9) → primaquine diphosphate (63-45-6)

Guidance literature:

N-phthalolylprimaquine; With hydrazine hydrate; In ethanol; at 78 - 80 ℃; Inert atmosphere;

Primaquine; With phosphoric acid; pyrographite; In ethanol; water; at 78 - 80 ℃; for 0.5h; Inert atmosphere; Darkness;

Reference yield:

Primaquine (90-34-6,57152-58-6) → primaquine diphosphate (63-45-6)

Guidance literature:

With phosphoric acid; In diethyl ether; Darkness;

DOI:10.1111/cbdd.12944

Reference yield:

4-methoxy-2-nitroaniline (96-96-8) → primaquine diphosphate (63-45-6)

Guidance literature:

Multi-step reaction with 5 steps

1: arsenic(V) oxide; phosphoric acid / 1 h / 100 °C / Darkness

2: hydrogen / 2585.81 Torr / Darkness

3: triethylamine / 6 h / 150 °C / Darkness

4: hydrazine / ethanol / 72 h / Reflux; Darkness

5: phosphoric acid / diethyl ether / Darkness

With arsenic(V) oxide; phosphoric acid; hydrogen; triethylamine; hydrazine; In diethyl ether; ethanol; 1: |Skraup Quinoline Synthesis;

DOI:10.1111/cbdd.12944

upstream raw materials:

Primaquine

4-methoxy-2-nitroaniline

6-methoxy-8-nitroquinoline

6-methoxyquinolin-8-amine

Downstream raw materials:

Primaquine

N-acetylprimaquin

Refernces

• 1、 Azad, Chandra S.,Saxena, Mridula,Siddiqui, Arif J.,Bhardwaj, Jyoti,Puri, Sunil K.,Dutta, Guru P.,Anand, Nitya,Saxena, Anil K.. "Synthesis of primaquine glyco-conjugates as potential tissue schizontocidal antimalarial agents". . p. 254 - 261. Retrieved 2017/07/13.