GSK1014802

Base Information

• Chemical Name: GSK1014802
• CAS No.: 934240-30-9
• Molecular Formula: C18H19FN2O2
• Molecular Weight: 314.359
• Mol file: 934240-30-9.mol

Synonyms:GSK1014802;CNV-1014802;(5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-L-prolinamide;GSK1014802(CNV1014802);MFCD22580419;(5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-L-prolinamide-HCL;(2S,5R)-5-[4-[(2-Fluorophenyl)methoxy]phenyl]-2-pyrrolidinecarboxamide;Raxatrigine

Chemical Property of GSK1014802

Chemical Property:

• Boiling Point: 529.5±50.0 °C(Predicted)
• PKA: 16.16±0.40(Predicted)
• PSA: 65.34000
• Density: 1.226±0.06 g/cm3(Predicted)
• LogP: 4.16160
• Solubility.: Soluble in DMSO

Purity/Quality:

99% ^*data from raw suppliers

Raxatrigine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Raxatrigine is used in the novel design for a phase IIa placebo-controlled, double-blind randomized withdrawal study to evaluate the safety and efficacy of CNV1014802 (novel sodium channel blocker) in patients with trigeminal neuralgia (unilateral facial discomfort).

Technology Process of GSK1014802

There total 17 articles about GSK1014802 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: 95.6%

tert-butyl (2S,5R)-2-carbamoyl-5-(4-((2-fluorobenzyl)oxy)-phenyl)pyrrolidine-1-carboxylate (934240-45-6) → (2S,5R)-5-(4-((2-fIuorobenzyl)oxy)phenyl)pyrrolidine-2-carboxamide (934240-30-9)

Guidance literature:

With methanesulfonic acid; In acetonitrile; at 40 - 50 ℃; Large scale;

DOI:10.1021/acs.oprd.0c00427

Reference yield: 93.7%

(2S,5R)-methyl-5-(4-((2-fluorobenzyl)oxy)phenyl)pyrrolidine-2-carboxylate p-toluenesulfonate salt → (2S,5R)-5-(4-((2-fIuorobenzyl)oxy)phenyl)pyrrolidine-2-carboxamide (934240-30-9)

Guidance literature:

(2S,5R)-methyl-5-(4-((2-fluorobenzyl)oxy)phenyl)pyrrolidine-2-carboxylate p-toluenesulfonate salt; With ammonium hydroxide; In tert-butyl methyl ether; water; at 30 ℃; for 0.5h; Large scale;

With ammonia; In methanol; at 3 - 30 ℃; for 24h; Large scale;

DOI:10.1021/acs.oprd.0c00382

Reference yield: 90.0%

(2S,5R)-methyl-5-(4-((2-fluorobenzyl)oxy)phenyl)pyrrolidine-2-carboxylate (934240-62-7) → (2S,5R)-5-(4-((2-fIuorobenzyl)oxy)phenyl)pyrrolidine-2-carboxamide (934240-30-9)

Guidance literature:

With ammonia; In methanol; for 96h; Concentration;

upstream raw materials:

(2S,5R)-methyl-5-(4-((2-fluorobenzyl)oxy)phenyl)pyrrolidine-2-carboxylate

o-fluorobenzyl bromide

methyl 4-hydroxylbenzoate

4-(2-fluorobenzyloxy)-N-methyl-N-methoxybenzamide

Downstream raw materials:

(5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-L-prolinamide methanesulfonate

(2S,5R)-5-(4-((2-fluorobenzyl)oxy)phenyl)pyrrolidine-2-carboxamide monohydrochloride

Refernces

• 1、 Giblin, Gerard,Heseltine, Adrian,Kiesman, William,Macpherson, David,Ramsden, James,Vadali, Ravi,Williams, Michael,Witty, David. "Synthesis of Vixotrigine, a Use-Dependent Sodium Channel Blocker. Part 1: Development of Bulk Supply Routes to Enable Proof of Concept". . p. 2802 - 2813. Retrieved 2020/12/22.
• 2、 -. "PROCESS FOR PREPARING ALPHA-CARBOXAMIDE PYRROLIDINE DERIVATIVES". Page/Page column 41. . Retrieved 2016/07/27.