CEP 33779

Base Information

• Chemical Name: CEP 33779
• CAS No.: 1257704-57-6
• Molecular Formula: C24H26N6O2S
• Molecular Weight: 462.575
• Mol file: 1257704-57-6.mol

Synonyms:[8-(4-Methylsulfonylphenyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl][3-(4-methylpiperazin-1-yl)phenyl]amine;

Chemical Property of CEP 33779

Chemical Property:

• PKA: 7.78±0.42(Predicted)
• PSA: 94.45000
• Density: 1.35
• LogP: 3.80080
• Solubility.: ≥23.15 mg/mL in DMSO with gentle warming; insoluble in EtOH

Purity/Quality:

99% min ^*data from raw suppliers

CEP-33779 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Janus kinases (JAKs) are non-receptor kinases that mediate signaling through cytokine receptors, often to members of the signal transducer and activator of transcription family. CEP-33779 is a potent, orally available inhibitor of JAK2 (IC50 = 1.3 nM). It shows 65-fold selectivity for JAK2 over JAK3. In mouse models of systemic lupus erythematosus, CEP-33779 reduces the production of inflammatory cytokines, decreases splenomegaly and lymphomegaly, and extends survival. It also diminishes inflammatory signaling and improves clinical scores in mice during collagen antibody-induced arthritis and collagen type II-induced arthritis. CEP-33779 induces regression of established colorectal tumors in mice, reducing angiogenesis and proliferation of tumor cells.
• Uses: CEP-33779 acts as an orally available inhibitor of JAK2 reducing the production of inflammatory cytokines and decreasing splenomegaly. Anti-arthritic agent. Anticancer agent.

Technology Process of CEP 33779

There total 11 articles about CEP 33779 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: 60.0%

→ {[8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]-pyridin-2-yl]-[3-(4-methyl-piperazin-1-yl)-phenyl]-amine} (1257704-57-6,1346168-57-7)

Guidance literature:

Reference yield: 36.0%

1-bromo-3-(4-methylpiperazin-1-yl)benzene (747413-17-8) + 8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5,a]-pyridine-2-ylamine (1257704-13-4) → {[8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]-pyridin-2-yl]-[3-(4-methyl-piperazin-1-yl)-phenyl]-amine} (1257704-57-6,1346168-57-7)

Guidance literature:

With dicyclohexyl-({2-[2-(dicyclohexylphosphanyl)phenyl]-phenyl})-phosphane; palladium diacetate; caesium carbonate; In 1,4-dioxane; at 100 ℃; for 72h; Inert atmosphere;

DOI:10.1021/jm300248q

Reference yield:

2-Amino-3-bromopyridine (13534-99-1) → {[8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]-pyridin-2-yl]-[3-(4-methyl-piperazin-1-yl)-phenyl]-amine} (1257704-57-6,1346168-57-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,4-dioxane / 18 h / Inert atmosphere

1.2: 20 h / 20 - 60 °C / Inert atmosphere

2.1: palladium diacetate; sodium carbonate; triphenylphosphine / 1,4-dioxane; water / 80 °C

3.1: dicyclohexyl-({2-[2-(dicyclohexylphosphanyl)phenyl]-phenyl})-phosphane; palladium diacetate; caesium carbonate / 1,4-dioxane / 72 h / 100 °C / Inert atmosphere

With dicyclohexyl-({2-[2-(dicyclohexylphosphanyl)phenyl]-phenyl})-phosphane; palladium diacetate; sodium carbonate; caesium carbonate; triphenylphosphine; In 1,4-dioxane; water; 2.1: Suzuki coupling / 3.1: Buchwald-Hartwig coupling;

DOI:10.1021/jm300248q

upstream raw materials:

1-bromo-3-(4-methylpiperazin-1-yl)benzene

8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5,a]-pyridine-2-ylamine

2-Amino-3-bromopyridine

8-bromo-[1,2,4]triazolo[1,5-a]pyridine-2-ylamine

Refernces

• 1、 -. "JANUS KINASE 2 (JAK2) INHIBITOR FOR THE TREATMENT OF LUPUS". Paragraph 0047. . Retrieved 2016/08/17.
• 2、 -. "PREPARATION AND USES OF 1,2,4-TRIAZOLO [1,5a] PYRIDINE DERIVATIVES". Page/Page column 154; 155. . Retrieved 2010/12/29.