(S)-[2,8-bis(trifluoromethyl)quinolin-4-yl]-[(2S)-piperidin-2-yl]methanol

Base Information

• Chemical Name: (S)-[2,8-bis(trifluoromethyl)quinolin-4-yl]-[(2S)-piperidin-2-yl]methanol
• CAS No.: 51744-85-5
• Molecular Formula: C₁₇H₁₆F₆N₂O*ClH
• Molecular Weight: 414.778
• UNII: GB2GL4S36Z
• DSSTox Substance ID: DTXSID901146248
• Nikkaji Number: J535.494C
• Wikipedia: Mefloquine
• NCI Thesaurus Code: C61827
• RXCUI: 6694
• ChEMBL ID: CHEMBL411685
• Mol file: 51744-85-5.mol

Synonyms:Lariam;Mefloquine;Mefloquine Hydrochloride;Mephloquine;Ro 21 5998 001;Ro-21-5998-001;Ro215998001;WR 142,490;WR 177,602;WR-142,490;WR-177,602;WR142,490;WR177,602

Chemical Property of (S)-[2,8-bis(trifluoromethyl)quinolin-4-yl]-[(2S)-piperidin-2-yl]methanol

Chemical Property:

• Vapor Pressure: 1.18E-07mmHg at 25°C
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 2
• Exact Mass: 378.11668211
• Heavy Atom Count: 26
• Complexity: 483

Purity/Quality:

98%min ^*data from raw suppliers

threo-MefloquineHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Drug Classes: Antimalarial Agents
• Canonical SMILES: C1CCNC(C1)C(C2=CC(=NC3=C2C=CC=C3C(F)(F)F)C(F)(F)F)O
• Isomeric SMILES: C1CCN[C@@H](C1)[C@H](C2=CC(=NC3=C2C=CC=C3C(F)(F)F)C(F)(F)F)O
• Recent ClinicalTrials: Temozolomide, Memantine Hydrochloride, Mefloquine, and Metformin Hydrochloride in Treating Patients With Glioblastoma Multiforme After Radiation Therapy
• Recent EU Clinical Trials: Pilot study to evaluate the efficacy and safety of mefloquine as prophylaxis in people exposed to the disease caused by the SARS-CoV-2 coronavirus (COVID-19)
• Recent NIPH Clinical Trials: The efficacy and safety of mefloquine in patients with progressive multifocal leukoencephalopathy
• Uses: threo-Mefloquine is a derivative of Mefloquine (M207050), a quinoline methanol antimalarial agent.

Technology Process of (S)-[2,8-bis(trifluoromethyl)quinolin-4-yl]-[(2S)-piperidin-2-yl]methanol

There total 12 articles about (S)-[2,8-bis(trifluoromethyl)quinolin-4-yl]-[(2S)-piperidin-2-yl]methanol 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: 95.0%

(+)-threo-mefloquine → (+)-threo-mefloquine hydrochloride (51744-85-5,68682-28-0)

Guidance literature:

With hydrogenchloride; water; In methanol; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201303931

Reference yield: 71.0%

(S)-(+)-[2,8-bis(trifluoromethyl)-4-quinolinyl]-2-pyridinylmethanol → (+)-threo-mefloquine hydrochloride (51744-85-5,68682-28-0) + (R)-2-((S)-(2,8-bis(trifluoromethyl)quinolin-4-yl)(hydroxy)methyl)piperidin-1-ium chloride (68682-28-0)

Guidance literature:

With hydrogenchloride; platinum on carbon; hydrogen; In methanol; at 25 ℃; for 24h; under 1500.15 Torr; Autoclave; Inert atmosphere;

DOI:10.1002/adsc.201300531

Reference yield:

(2,8-bis-trifluoromethyl)-4-bromoquinoline (35853-45-3) → (+)-threo-mefloquine hydrochloride (51744-85-5,68682-28-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / -78 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: (R,Rp)-1-(2-(diphenylphosphano)ferrocenyl)-1-(2-diphenylphosphanophenyl)-N,N-dimethylmethanamine; palladium diacetate; N,N-dimethyl-aniline / 1,4-dioxane / 12 h / 25 °C / Inert atmosphere

2.2: 2 h / 130 °C / Inert atmosphere; Microwave irradiation

3.1: Crabtree's catalyst; hydrogen / dichloromethane / 48 h / 20 °C / 760.05 Torr / Inert atmosphere

4.1: hydrogenchloride; water / methanol / 1 h / 20 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; Crabtree's catalyst; (R,Rp)-1-(2-(diphenylphosphano)ferrocenyl)-1-(2-diphenylphosphanophenyl)-N,N-dimethylmethanamine; water; hydrogen; palladium diacetate; N,N-dimethyl-aniline; In 1,4-dioxane; methanol; dichloromethane;

DOI:10.1002/anie.201303931

upstream raw materials:

(2,8-bis-trifluoromethyl)-4-bromoquinoline

2,8-bis(trifluoromethyl)-4-quinoline carboxaldehyde

[2,8-bis(trifluoromethyl)-4-quinolinyl]-2-pyridinylmethanone