Pamapimod

Base Information

• Chemical Name: Pamapimod
• CAS No.: 449811-01-2
• Molecular Formula: C19H20 F2 N4 O4
• Molecular Weight: 406.389
• Hs Code.: 2933998090
• UNII: 8S2C9V11K4
• ChEMBL ID: CHEMBL1090089
• DSSTox Substance ID: DTXSID90963312
• NCI Thesaurus Code: C90996
• Pharos Ligand ID: 171LZC4Y7XCH
• Wikidata: Q27162644
• Mol file: 449811-01-2.mol

Synonyms:pamapimod

Chemical Property of Pamapimod

Chemical Property:

• PSA: 112.73000
• LogP: 1.36620
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 406.14526146
• Heavy Atom Count: 29
• Complexity: 591

Purity/Quality:

97% ^*data from raw suppliers

Pamapimod ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=NC(=NC=C2C=C(C1=O)OC3=C(C=C(C=C3)F)F)NC(CCO)CCO
• Recent EU Clinical Trials: An 8-week double-blind, randomized, placebo-controlled, phase II study evaluating the effects of oral pamapimod 150 mg with pioglitazone 10 mg daily on COVID-19 development in hospitalized patients infected with SARS-CoV-2 (severe acute respiratory syndrome-coronavirus-2)
• Uses: A selective inhibitor of the α-isoform of p38 MAP kinase A selective inhibitor of the α-isoform of p38 MAP kinase. It is used in in treatment of patient with rheumatoid arthritis. Pamapimod was tolerable but not effective as Methotrexate.

Technology Process of Pamapimod

There total 8 articles about Pamapimod 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: 93.0%

6-(2,4-difluorophenoxy)-8-methyl-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one (449808-50-8) + 3-trimethylsilanyloxy-1-(2-trimethylsilanyloxyethyl)propylamine (1032451-78-7) → [14C]-Pamapimod (449811-01-2)

Guidance literature:

6?(2,4?difluorophenoxy)?8?methyl?2?(methylsulfonyl)pyrido[2,3?d]pyrimidin?7(8H)?one; 3-trimethylsilanyloxy-1-(2-trimethylsilanyloxyethyl)propylamine; With N,O-bis-(trimethylsilyl)-acetamide; In tetrahydrofuran; Reflux;

With potassium dihydrogenphosphate; water; In tert-butyl methyl ether;

DOI:10.1021/jm101423y

Reference yield:

6?(2,4?difluorophenoxy)?8?methyl?2?(methylthio)pyrido[2,3?d]pyrimidin?7(8H)?one (449811-12-5) → [14C]-Pamapimod (449811-01-2)

Guidance literature:

Multi-step reaction with 2 steps

1: formic acid; dihydrogen peroxide / dichloromethane; water / 38 °C

2: N,O-bis-(trimethylsilyl)-acetamide / tetrahydrofuran / Reflux

With formic acid; N,O-bis-(trimethylsilyl)-acetamide; dihydrogen peroxide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jm101423y

Reference yield:

(4-methylamino-2-methylsulfanyl-pyrimidin-5-yl)-methanol (17759-30-7) → [14C]-Pamapimod (449811-01-2)

Guidance literature:

Multi-step reaction with 4 steps

1: manganese(IV) oxide / dichloromethane / 24 h

2: potassium carbonate / 1-methyl-pyrrolidin-2-one / 18 h / 120 °C

3: formic acid; dihydrogen peroxide / dichloromethane; water / 38 °C

4: N,O-bis-(trimethylsilyl)-acetamide / tetrahydrofuran / Reflux

With manganese(IV) oxide; formic acid; N,O-bis-(trimethylsilyl)-acetamide; dihydrogen peroxide; potassium carbonate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; dichloromethane; water;

DOI:10.1021/jm101423y

upstream raw materials:

6-(2,4-difluorophenoxy)-8-methyl-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one

3-trimethylsilanyloxy-1-(2-trimethylsilanyloxyethyl)propylamine

6?(2,4?difluorophenoxy)?8?methyl?2?(methylthio)pyrido[2,3?d]pyrimidin?7(8H)?one

(4-methylamino-2-methylsulfanyl-pyrimidin-5-yl)-methanol