4-(Chloromethyl)-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)benzamide

Base Information

• Chemical Name: 4-(Chloromethyl)-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)benzamide
• CAS No.: 404844-11-7
• Molecular Formula: C24H20ClN5O
• Molecular Weight: 429.909
• DSSTox Substance ID: DTXSID30436494
• Nikkaji Number: J3.130.643D
• Wikidata: Q72454291
• ChEMBL ID: CHEMBL1765715
• Mol file: 404844-11-7.mol

Synonyms:404844-11-7;4-(Chloromethyl)-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)benzamide;4-Chloromethyl-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]benzamide;N-[4-Methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-4-chloromethyl Benzamide;4-(chloromethyl)-N-[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]benzamide;CHEMBL1765715;4-(CHLOROMETHYL)-N-(4-METHYL-3-{[4-(PYRIDIN-3-YL)PYRIMIDIN-2-YL]AMINO}PHENYL)BENZAMIDE;4-(chloromethyl)-n-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)benzamide;4-(Chloromethyl)-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]benzamide;4-(chloromethyl)-N-{4-methyl-3-[4-(pyridin-3-yl)pyrimidin-2-ylamino]phenyl}benzamide;4-chloromethyl-N-(4-methyl-3-((4-pyridin-3-yl)-pyrimidin-2-ylamino)-phenyl)-benzamide;4-chloromethyl-N-{4-methyl-3-[(4-pyridin-3-yl)-pyrimidin-2-ylamino]-phenyl}-benzamide;N-(5-(4-chloromethylbenzoylamino)-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine-amine;N-[5-(4-chloromethylbenzoylamino)-2-methylphenyl]-4-(3-pyridyl)-2-pyrimidine-amine;SCHEMBL723757;DTXSID30436494;BDBM50341234;MFCD09841001;VCC748774;AKOS015896091;AC-5912;AT23819;DS-6634;PD119309;AM20090631;CS-0205716;FT-0659510;A825129;4-(Chloromethyl)-N-(4-methyl-3-{[4-(3-pyridinyl)-2-pyrimidinyl]amino}phenyl)benzamide;4-chloromethyl-N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)benzamide;4-chloromethyl-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide;4-chloromethyl-N-[4-methyl-3-(4-pyridin-3-yl-pyrmidin-2-ylamino)-phenyl]-benzamide;4-chloromethyl-N-[4-methyl-3-(4-pyridine-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide;Benzamide, 4-(chloromethyl)-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-;n-(5-(4-chloromethylbenzoylamino)-2-methylphenyl)-4-(3-pyridyl)-2-pyrimdine-amine;N-[3-[[4-(3-Pyridinyl)pyrimidine-2-yl]amino]-4-methylphenyl]-4-(chloromethyl)benzamide;4-(chloromethyl)-N-[4-methyl-3-[[4-(3-pyridyl)pyrimidin-2-yl]amino]phenyl]benzamide;Chloromethyl-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]Amino]phenyl]benzamide Intermediate of Imatinib Mesylate

Chemical Property of 4-(Chloromethyl)-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)benzamide

Chemical Property:

• Appearance/Colour: Off-white solid
• Melting Point: 300 °C (dec)
• Refractive Index: 1.691
• PKA: 12.99±0.70(Predicted)
• PSA: 79.80000
• Density: 1.33 g/cm³
• LogP: 5.72770
• Storage Temp.: -20°C Freezer
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 429.1356380
• Heavy Atom Count: 31
• Complexity: 570

Purity/Quality:

99.0%, High purity. ^*data from raw suppliers

N-[4-Methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-4-chloromethylBenzamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=C(C=C1)NC(=O)C2=CC=C(C=C2)CCl)NC3=NC=CC(=N3)C4=CN=CC=C4
• Uses: Gleevec Impurity

Technology Process of 4-(Chloromethyl)-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)benzamide

There total 17 articles about 4-(Chloromethyl)-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)benzamide 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: 99.0%

p-(chloromethyl)benzoyl chloride (876-08-4) + 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine (152460-10-1) → 4-(chloromethyl)-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]-amino}phenyl)benzamide (404844-11-7)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 0 - 20 ℃; for 4h;

DOI:10.1002/cmdc.201700044

Reference yield:

p-(chloromethyl)benzoic acid (1642-81-5) + 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine (152460-10-1) → 4-(chloromethyl)-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]-amino}phenyl)benzamide (404844-11-7)

Guidance literature:

p-(chloromethyl)benzoic acid; With thionyl chloride; In 1,4-dioxane; N,N-dimethyl-formamide; at 65 - 70 ℃; for 10 - 12h;

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine; With pyridine; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; at -5 - 5 ℃; for 1 - 1.5h;

Reference yield:

N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine (152460-09-8) → 4-(chloromethyl)-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]-amino}phenyl)benzamide (404844-11-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 8.9 g / SnCl₂; aq. HCl / 0.5 h

2: 61 percent / dimethylformamide / 2 h / 0 °C

With hydrogenchloride; tin(ll) chloride; In N,N-dimethyl-formamide;

DOI:10.1021/jm049546c

upstream raw materials:

p-(chloromethyl)benzoyl chloride

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

methyl-3-pyridylketone

3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one

Downstream raw materials:

N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)-4-(piperidin-1-ylmethyl)benzamide

imatinib mesylate

4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[[4-(3-pyridinyl)-2-pyrimidinyl]-N-acetyl]amino]phenyl]benzamide

Refernces

• 1、 -. "Synthesis method of imatinib and imatinib mesylate". Paragraph 0096-0102. . Retrieved 2020/05/02.
• 2、 Sun, Weilin,Netzer, William J.,Sinha, Anjana,Gindinova, Katherina,Chang, Emily,Sinha, Subhash C.. "Development of Gleevec Analogues for Reducing Production of β-Amyloid Peptides through Shifting β-Cleavage of Amyloid Precursor Proteins". supporting information. p. 3122 - 3134. Retrieved 2019/04/01.