Allitinib metabolite M6

Base Information

• Chemical Name: Allitinib metabolite M6
• CAS No.: 845271-71-8
• Molecular Formula: C₂₁H₁₆ClFN₄O
• Molecular Weight: 394.836
• UNII: 9XRF7KN4QK
• DSSTox Substance ID: DTXSID301346050
• ChEMBL ID: CHEMBL3637893
• Mol file: 845271-71-8.mol

Synonyms:Allitinib metabolite M6;9XRF7KN4QK;UNII-9XRF7KN4QK;845271-71-8;MMV688273;N-(3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)quinazoline-4,6-diamine;4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-aminoquinazoline;N4-(3-Chloro-4-((3-fluorophenyl)methoxy)phenyl)-4,6-quinazolinediamine;4,6-Quinazolinediamine, N4-(3-chloro-4-((3-fluorophenyl)methoxy)phenyl)-;SCHEMBL233913;CHEMBL3637893;FBSYJUVNGAMMOK-UHFFFAOYSA-N;DTXSID301346050;PD061215;SR-05000022762;SR-05000022762-1;4-[3-chloro-4-(3-fluoro-benzyloxy)-phenylamino]-6-amino-quinazoline;4-N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]quinazoline-4,6-diamine;N4-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)quinazoline-4,6-diamine;N4-[3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-quinazolin-4,6-diamine;N4-[3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-quinazoline-4,6-diamine

Chemical Property of Allitinib metabolite M6

Chemical Property:

• XLogP3: 4.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 394.0996670
• Heavy Atom Count: 28
• Complexity: 501

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)F)COC2=C(C=C(C=C2)NC3=NC=NC4=C3C=C(C=C4)N)Cl

Technology Process of Allitinib metabolite M6

There total 16 articles about Allitinib metabolite M6 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: 97.0%

[3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-(6-nitro-quinazolin-4-yl)-amine (851653-35-5) → N4-[3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-quinazoline-4,6-diamine (845271-71-8)

Guidance literature:

With iron; calcium chloride; In ethanol; water; at 90 ℃; for 12h;

DOI:10.1021/acs.jmedchem.0c01647

Reference yield: 83.0%

[3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-(6-nitro-quinazolin-4-yl)-amine hydrochloride (851545-72-7) → N4-[3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-quinazoline-4,6-diamine (845271-71-8)

Guidance literature:

[3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-(6-nitro-quinazolin-4-yl)-amine hydrochloride; With hydrogenchloride; indium; In tetrahydrofuran; water; at 0 - 20 ℃; for 10.5h;

With sodium hydrogencarbonate; In water; for 0.5h;

Reference yield:

GLUTATHIONE (70-18-8) + allitinib epoxide (1636145-49-7) → N4-[3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-quinazoline-4,6-diamine (845271-71-8) + C33H33ClFN7O9S + 27,28-dihydrodiolallitinib (1469980-18-4)

Guidance literature:

With ethylenediaminetetraacetic acid; magnesium chloride; In aq. phosphate buffer; dimethyl sulfoxide; at 37 ℃; for 1h; pH=7.4; Enzymatic reaction;

DOI:10.1124/dmd.113.056341

upstream raw materials:

[3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-(6-nitro-quinazolin-4-yl)-amine hydrochloride

[3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-(6-nitro-quinazolin-4-yl)-amine

4-chloro-6-nitro-quinazoline

3-chloro-4-(3-fluorobenzyloxy)aniline

Downstream raw materials:

N-4-[3-chloro-4-(3-fluorobenzyloxy)-phenyl]-N-6-(2-phenyl-N-cyanoisourea)-quinazoline-4,6-diamine

N-{4-[3-chloro-4-(3-fluorobenzyloxy)-phenylamino]-quinazolin-6-yl}-4-methylbenzenesulfonamide

N-(4-(4-(3-fluorobenzyloxy)-3-chlorophenylamino)quinazolin-6-yl)acrylamide

(E)-4-morpholin-4-yl-but-2-enoic [carbonyl-¹¹C]acid {4-[3-chloro-4-(3-fluoro-benzyloxy)-phenylamino]-quinazolin-6-yl}-amide

Refernces

• 1、 Elwaie, Tamer A.,Abbas, Safinaz E.,Aly, Enayat I.,George, Riham F.,Ali, Hamdy,Kraiouchkine, Nikolai,Abdelwahed, Khaldoun S.,Fandy, Tamer E.,El Sayed, Khalid A.,Abd Elmageed, Zakaria Y.,Ali, Hamed I.. "HER2 Kinase-Targeted Breast Cancer Therapy: Design, Synthesis, and in Vitro and in Vivo Evaluation of Novel Lapatinib Congeners as Selective and Potent HER2 Inhibitors with Favorable Metabolic Stability". . p. 15906 - 15945. Retrieved 2021/01/09.
• 2、 Lin, Songwen,Li, Yingbo,Zheng, Yufen,Luo, Laichun,Sun, Qi,Ge, Zemei,Cheng, Tieming,Li, Runtao. "Design, synthesis and biological evaluation of quinazoline–phosphoramidate mustard conjugates as anticancer drugs". . p. 442 - 458. Retrieved 2017/01/18.