GZD 824

Base Information

• Chemical Name: GZD 824
• CAS No.: 1257628-77-5
• Molecular Formula: C29H27F3N6O
• Molecular Weight: 532.568
• Mol file: 1257628-77-5.mol

Synonyms:GZD824;GZD8824;GZD-824;GZD 824;GZD-824 Free;Olverembatinib;GZD 824 USP/EP/BP;GZD824;GZD-824;GZD 824;Olverembatinib (GZD824);GZD-824; GZD 824;BENZAMIDE

Chemical Property of GZD 824

Chemical Property:

• Boiling Point: 630.4±55.0 °C(Predicted)
• PKA: 9.04±0.40(Predicted)
• PSA: 77.15000
• Density: 1.39±0.1 g/cm3(Predicted)
• LogP: 4.63340

Purity/Quality:

98% min ^*data from raw suppliers

GZD824 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: GZD-824 is an orally available inhibitor of a broad spectrum of Bcr/Abl tyrosine kinase mutants including T315I (IC50s = 0.34 and 0.68 nM for wild-type Bcr/Abl and Bcr/AblT315I, respectively). It has been shown to suppress the proliferation of Bcr/Abl-positive K562 and Ku812 human chronic myelogenous leukemia cells (IC50s = 0.2 and 0.13 nM, respectively) and induce tumor regression in mouse xenograft tumor models driven by either wild-type or mutant Bcr/Abl.
• Uses: GZD824 is a orally bioavailable inhibitor that targets phosphorylated and non-phosphorylated Breakpoint Cluster Region-Abelson (Bcr-Abl) kinases. It is a COVID19-related research product.

Technology Process of GZD 824

There total 8 articles about GZD 824 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: 95.56%

4-(4-methylpiperazin-1-ylmethyl)-3-trifluoromethylaniline (694499-26-8) + C17H13N3O2 → 3-(2-(1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide (1257628-77-5)

Guidance literature:

With triethylamine; In tetrahydrofuran; at -60 - -40 ℃; for 2h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

Reference yield: 76.0%

3-iodo-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl) phenyl)benzamide (943320-50-1) + 5-ethynyl-1H-pyrazolo[3,4-b]pyridine (1207351-15-2) → 3-(2-(1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide (1257628-77-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In acetonitrile; at 20 - 100 ℃; for 20h; Sealed tube; Inert atmosphere;

DOI:10.1021/jm301581y

Reference yield:

methyl 3-iodo-4-methylbenzoate (90347-66-3) → 3-(2-(1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide (1257628-77-5)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium tert-butylate / tetrahydrofuran / 3 h / -20 - 20 °C / Inert atmosphere

2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / acetonitrile / 20 h / 20 - 100 °C / Sealed tube; Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium tert-butylate; triethylamine; In tetrahydrofuran; acetonitrile; 2: |Sonogashira Cross-Coupling;

DOI:10.1021/jm301581y

upstream raw materials:

3-iodo-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl) phenyl)benzamide

5-ethynyl-1H-pyrazolo[3,4-b]pyridine

methyl 3-iodo-4-methylbenzoate

4-(4-methylpiperazin-1-ylmethyl)-3-trifluoromethylaniline

Downstream raw materials:

3-((1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide bismethanesulfonic acid

Refernces

• 1、 -. "A PROCESS FOR PREPARING ALKYNYL-CONTAINING COMPOUND AND INTERMEDIATE THEREOF". Paragraph 00127; 00131; 00132; 00135. . Retrieved 2021/08/27.
• 2、 -. "HETEROCYCLIC ALKYNYL BENZENE COMPOUNDS AND MEDICAL COMPOSITIONS AND USES THEREOF". Paragraph 0122; 0123; 0124. . Retrieved 2013/06/05.