4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid ethyl ester

Base Information

• Chemical Name: 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid ethyl ester
• CAS No.: 641569-97-3
• Molecular Formula: C₁₉H₁₈N₄O₂
• Molecular Weight: 334.378
• Hs Code.: 2933990090
• Mol file: 641569-97-3.mol

Synonyms:4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoicacid ethyl ester;Ethyl 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoate;

Chemical Property of 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid ethyl ester

Chemical Property:

• Boiling Point: 546.1 °C at 760 mmHg
• Flash Point: 284.1 °C
• PSA: 77.00000
• Density: 1.233 g/cm³
• LogP: 3.84030
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

98% ^*data from raw suppliers

Ethyl4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic Acid Ethyl Ester-D6 is an intermediate in the synthesis of Nilotinib-d6 (N465303), which is the labeled analogue of Nilotinib, which might be useful in treatment of chronic myelogenous leukemia. Ethyl 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoate is used in preparation of the Smo inhibitor and synthesis and their application.

Technology Process of 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid ethyl ester

There total 13 articles about 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid ethyl ester 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: 90.0%

3-amino-4-methylbenzoic acid ethyl ester (41191-92-8) + 2-chloro-4-(pyridin-3-yl)pyrimidine (483324-01-2) → 4-methyl-3-[[4-(3-pyridyl)-2-pyrimidinyl]amino]benzoic acid ethyl ester (641569-97-3)

Guidance literature:

With methanesulfonic acid; In isopropyl alcohol; at 100 ℃; for 30h; Temperature; Solvent; Reagent/catalyst;

Reference yield: 73.4%

3-guanidino-4-methylbenzoic acid ethyl ester nitrate (641569-96-2) + 3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one (55314-16-4,75415-01-9,123367-26-0) → 4-methyl-3-[[4-(3-pyridyl)-2-pyrimidinyl]amino]benzoic acid ethyl ester (641569-97-3)

Guidance literature:

With sodium hydroxide; In butan-1-ol; for 72h; Reflux; Inert atmosphere;

DOI:10.1111/cbdd.12272

Reference yield: 61.0%

C11H15N3O2 (641569-95-1) + 3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one (55314-16-4,75415-01-9,123367-26-0) → 4-methyl-3-[[4-(3-pyridyl)-2-pyrimidinyl]amino]benzoic acid ethyl ester (641569-97-3)

Guidance literature:

With N,N-diethyl-N-isopropylamine; In butan-1-ol; at 140 ℃;

DOI:10.2533/chimia.2019.561

upstream raw materials:

3-guanidino-4-methylbenzoic acid ethyl ester nitrate

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

3-amino-p-toluic acid

3-amino-4-methylbenzoic acid ethyl ester

Downstream raw materials:

N-(3-bromo-5-(trifluoromethyl)phenyl)-4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzamide

Refernces

• 1、 Manley, Paul W.. "Investigations into the potential role of metabolites on the anti-leukemic activity of imatinib, nilotinib and midostaurin". . p. 561 - 570. Retrieved 2019/09/03.
• 2、 -. "Smo inhibitor as well as synthesis method and application thereof". . . Retrieved 2019/09/17.