444731-75-3

Basic information

• Product Name: N-(2-chloropyriMidin-4-yl)-N,2,3-triMethyl-2H-indazol-6-aMine
• Synonyms: N-(2-chloropyriMidin-4-yl)-N,2,3-triMethyl-2H-indazol-6-aMine;N-(2-chloro-4-pyriMidinyl)-N,2,3-triMethyl-2H-indazol-6-aMine;2H-Indazol-6-aMine, N-(2-chloro-4-pyriMidinyl)-N,2,3-triMethyl-;6-[N-(2-chloro-4-pyriMidinyl)MethylaMino]-2,3-diMethyl-2H-indazole, 96%;N-(2-ChloropyriMidin-4-yl)-N-Methyl-2,3-diMethyl-2H-indazol-6-aMine;N-(2-chloropyrimidin-4-yl)-N,2,3-trimethylindazol-6-amine;Pazopanib Impurity 8
• CAS NO: 444731-75-3
• Molecular Formula: C₁₄H₁₄ClN₅
• Molecular Weight: 288
• EINECS: 1592732-453-0
• Mol File: 444731-75-3.mol
• Article Data: 23

Chemical Properties

• Melting Point: 167-173℃
• Boiling Point: 524.447 °C at 760 mmHg
• Flash Point: 270.976 °C
• Appearance: /
• Density: 1.339 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.673
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Very Slightly)
• PKA: 2.82±0.30(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: N-(2-chloropyriMidin-4-yl)-N,2,3-triMethyl-2H-indazol-6-aMine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-chloropyriMidin-4-yl)-N,2,3-triMethyl-2H-indazol-6-aMine(444731-75-3)
• EPA Substance Registry System: N-(2-chloropyriMidin-4-yl)-N,2,3-triMethyl-2H-indazol-6-aMine(444731-75-3)

Safety Data

• Hazardous Substances Data: 444731-75-3(Hazardous Substances Data)

Usage

Uses

N-(2-Chloro-4-pyrimidinyl)-N,2,3-trimethyl-2H-indazol-6-amine is an impurity of Pazopanib (P210925), an oral angiogenesis inhibitor targeting VEGFR and PDGFR.

InChI:InChI=1/C14H14ClN5/c1-9-11-5-4-10(8-12(11)18-20(9)3)19(2)13-6-7-16-14(15)17-13/h4-8H,1-3H3

Upstream product

• 444731-74-2 N-(2-chloropyrimidin-4-yl)-2,3-dimethyl-2H-indazol-6-amine 
• 616-38-6 carbonic acid dimethyl ester 
• 444731-66-2 N-(2-chloro-4-pyrimidinyl)-N-(3-methyl-1H-indazol-6-yl)amine 
• 74-88-4 methyl iodide 
• 1142189-49-8 6-bromo-2,3-dimethyl-1H-indazole 
• 90221-46-8 3-methyl-6-bromo-2H-indazole 
• 14922-91-9 2-ethyl-5-bromoaniline 
• 10342-66-2 4-bromo-1-ethyl-2-nitro-benzene 
• 612-22-6 2-nitro(ethylbenzene) 
• 7461-50-9 2-chloropyrimidin-4-amine 
• 1426675-40-2 6-chloro-2,3-dimethyl-2H-indazole 
• 635702-59-9 3-methyl-6-nitro-1H-indazole sulfate 
• 77-78-1 dimethyl sulfate 
• 1313372-75-6 3?methyl?6?nitro?1H?indazole 

Downstream Products

• 635702-65-7 5-({4-[(2,3-dimethyl-2H-indazol-6-yl)(methyl)amino]pyrimidin-2-yl}amino)-2-methylbenzenesulfonamide methanesulfonic acid salt 
• 635702-64-6 5-[[4-[(2,3-dimethyl-2H-indazol-6-yl)-N-methylamino]-2-pyrimidinyl]amino]-2-methylbenzenesulfonamide hydrochloride 

Relevant articles and documents

Preparation method of pazopanib intermediate

The invention provides a preparation method of a pazopanib key intermediate 2,3-dimethyl-N-(2-chloropyrimidin-4-yl)-N-methyl-2H-indazole-6-amine. The method comprises the following steps: by taking 6-halogenated-2,3-dimethyl-2H-indazole as a raw material, conducting reacting to obtain N,2,3-trimethyl-2H-indazole-6-amine; and further carrying out a reaction to obtain the 2,3-dimethyl-N-(2-chloropyrimidin-4-yl)-N-methyl-2H-indazole-6-amine. The method has the advantages of short synthesis route, accessible raw materials, low cost, mild reaction conditions, high safety and high yield, and is suitable for industrial mass production.

Green preparation method of palatinib hydrochloride (by machine translation)

The invention belongs to the technical field of chemical synthesis of medicines, and belongs to the technical field of pharmaceutical chemistry. The invention particularly relates to a green preparation method. The o-methyl aniline and N - chlorosuccinimide are chlorinated to obtain 2 - methyl -5 - chloro- aniline; the 6 - chlorine - 222H-indole hydrochloride is obtained by reacting with the nitrous acid compound; N-methyl -6 -chloro - 222H-indole; under the participation of dimethyl sulfoxide, 3 - 2-dimethyl 3 - chlorine -6 - 222H-indazole; and the like. A reaction with 2 - chloro -4 - amino - pyrimidine and iodomethane gave N - (2 -chloropyrimidine -4 -yl) - N N-methyl -2, 3 -dimethyl - 222H-indazole -6 - amine; and finally, a pimatinib hydrochloride salt was obtained by reaction with 3 - sulfanilide -4 - methyl - aniline. The method is low in raw material price, simple to operate, low in operation risk, capable of avoiding waste acid generation, high in reaction yield, and high in purity. (by machine translation)

Synthesis and characterization of four process impurities in pazopanib

Pazopanib (trade name Votrient) is a potent and selective multi-targeted tyrosine kinase inhibitor that blocks tumor growth and inhibits angiogenesis. Based on a recently reported procedure, we herein report the first synthesis of four potential process impurities generated in the production of pazopanib. The structure of these impurities were synthesized and characterized by 1H NMR, 13C NMR and HRMS data. The possible formation mechanisms of these impurities were also elucidated. These findings should be useful for the quality control of pazopanib in manufacture.