1213269-26-1

Basic information

• Product Name: 4-(3-aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1- yl)phenyl)pyrimidin-2-amine
• Synonyms: 4-(3-aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1- yl)phenyl)pyrimidin-2-amine;4-(3-aminophenoxy)-5-chloro-N-[2-methoxy-4-(4-methyl-1-piperazinyl)phenyl]-2-Pyrimidinamine
• CAS NO: 1213269-26-1
• Molecular Formula: C₂₂H₂₅ClN₆O₂
• Molecular Weight: 440.9259
• Mol File: 1213269-26-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 4-(3-aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1- yl)phenyl)pyrimidin-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1- yl)phenyl)pyrimidin-2-amine(1213269-26-1)
• EPA Substance Registry System: 4-(3-aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1- yl)phenyl)pyrimidin-2-amine(1213269-26-1)

Safety Data

• Hazardous Substances Data: 1213269-26-1(Hazardous Substances Data)

Upstream product

• 446-36-6 5-fluoro-2-nitrophenol 
• 448-19-1 4-fluoro-2-methoxy-1-nitrobenzene 
• 761440-26-0 2-methoxy-4-(4-methyl piperazin-1-yl)nitrobenzene 
• 109-01-3 1-methyl-piperazine 
• 1374641-73-2 tert-butyl (3-((2,5-dichloropyrimidin-4-yl) oxy) phenyl)carbamate 
• 122833-04-9 2-methoxy-4-(4-methylpiperazin-1-yl)aniline 
• 1213269-25-0 5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)-4-(3-nitrophenoxy)pyrimidin-2-amine 
• 19962-06-2 tert-butyl 3-hydroxyphenylcarbamate 
• 554-84-7 meta-nitrophenol 
• 76661-24-0 2,5-dichloro-4-(3-nitrophenoxy)pyrimidine 

Downstream Products

• 1213269-23-8 N-(3-(5-chloro-2-(2-methoxy-4-(4-methylpiperazin-1-yl)phenylamino)pyrimidin-4-yloxy)phenyl)acrylamide 
• 1588522-80-8 N-(3-((5-chloro-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)oxy)phenyl)-3-(dimethylamino)propanamide 
• 1588522-82-0 N-(3-((5-chloro-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)oxy)phenyl)-3-(diethylamino)propanamide 
• 1588522-84-2 N-(3-((5-chloro-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)oxy)phenyl)-3-(pyrrolidin-1-yl)propanamide 
• 1588522-86-4 N-(3-((5-chloro-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)oxy)phenyl)-3-(piperidin-1-yl)propanamide 
• 1588522-88-6 N-(3-((5-chloro-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)oxy)phenyl)-3-morpholinopropanamide 
• 1588522-90-0 N-(3-((5-chloro-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)oxy)phenyl)-3-(4-methylpiperazin-1-yl)propanamide 
• 1588522-92-2 ethyl-4-(3-((3-((5-chloro-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)oxy)phenyl)amino)-3-oxopropyl)piperazine-1-carboxylate 
• 1588522-94-4 N-(3-((5-chloro-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)oxy)phenyl)-3-(4-(2-hydroxyethyl)piperazin-1-yl)propanamide 
• 1588522-96-6 4-(2-(4-(3-((3-((5-chloro-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)oxy)phenyl)amino)-3-oxopropyl)piperazin-1-yl)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide 

Relevant articles and documents

Design, synthesis and SAR study of 2-aminopyrimidines with diverse Michael addition acceptors for chemically tuning the potency against EGFRL858R/T790M

The covalent binding nature of irreversible kinase inhibitors potentially increases the severity of “off-target” toxicity. Based on our continual strategy of chemically tuning the Michael addition acceptors, herein, we further explore the relationship amo

Design, synthesis and biological evaluation of WZ4002 analogues as EGFR inhibitors

A series of thirty two anilinopyrimidines derived from WZ4002 has been synthesized and evaluated for percentage inhibition of six different EGFR kinases using LanthaScreen binding assay method (EGFR d746 – 750) or Z'LYTE assay method (EGFR-WT, EGFR d746 – 750, EGFR T790M, EGFR T790M L858R, EGFR C797S and EGFR T790M L858R C797S). Ortho-hydroxyacetamide 10 exhibited complete inhibition of all the six kinases at 10 μM. Against the triple mutant, EGFR T790M C797S L858R, compounds 9–12 exhibited complete inhibition at 10 μM and nearly complete inhibition at 1 μM. The target compounds were also evaluated using the MTT assay to determine their cytotoxic activity against human non-small cell lung cancer cells (PC9, PC9GR and H460) and mouse leukemic cells (Ba/F3 WT and Ba/F3T 3151). Overall, 7, 9–12, 30 and 31 were found to be the most potent compounds across all five cell lines.

Synthesis and evaluation of 2-anilinopyrimidines bearing 3-aminopropamides as potential epidermal growth factor receptor inhibitors

Novel compounds 12a-i were synthesized and biologically evaluated. Several ones exhibited stronger inhibitory activity than gefitinib against EGFR L858R/T790M and antiproliferative effects on H1975 and HCC827 cells. The 3-aminopropamide in compounds like 12h could be converted to the active acrylamide in the presence of arginine. Importantly, 12h showed improved stability relative to compound 1 whose structure is same to 12h excepting an acrylamide moiety. Interestingly, 12i, a NO donating compound of 12h, showed more potent and selective inhibition than 12h on H1975 cells. Significantly, 12i produced high levels of NO in H1975 cells but not in non-tumorous 16HBE cells, and its inhibition was diminished by NO scavenger. Furthermore, 12i dose-dependently produced inhibitory effects on EGFR downstream signaling in H1975 cells.