444731-72-0

Basic information

• Product Name: 2,3-DIMETHYL-2H-INDAZOL-6-AMINE
• Synonyms: 2,3-DIMETHYL-2H-INDAZOL-6-AMINE;6-Amino-2,3-dimethyl-2H-indazole;2,3-dimethyl-2H-indazol-6-ylamine;2,3-Dimethyl-6-amino-2H-indazole;6-Amino-2,3-dimethyl-2H-i...;2H-Indazol-6-aMine, 2,3-diMethyl-;3-Dimethyl-2H-indazol-6-amine
• CAS NO: 444731-72-0
• Molecular Formula: C₉H₁₁N₃
• Molecular Weight: 161.2
• Mol File: 444731-72-0.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 366.91 °C at 760 mmHg
• Flash Point: 175.701 °C
• Appearance: /
• Density: 1.232 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.645
• PKA: 4.20±0.30(Predicted)
• CAS DataBase Reference: 2,3-DIMETHYL-2H-INDAZOL-6-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIMETHYL-2H-INDAZOL-6-AMINE(444731-72-0)
• EPA Substance Registry System: 2,3-DIMETHYL-2H-INDAZOL-6-AMINE(444731-72-0)

Safety Data

• Hazardous Substances Data: 444731-72-0(Hazardous Substances Data)

Usage

Uses

2,3-Dimethyl-6-amino-2H-indazole is an impurity in the synthesis of Pazopanib (P210925) hydrochloride, an oral angiogenesis inhibitor targeting VEGFR and PDGFR.

InChI:InChI=1/C9H11N3/c1-6-8-4-3-7(10)5-9(8)11-12(6)2/h3-5H,10H2,1-2H3

Upstream product

• 1313372-75-6 3?methyl?6?nitro?1H?indazole 
• 612-22-6 2-nitro(ethylbenzene) 
• 6494-19-5 3-methyl-6-nitro-1H-indazole 
• 74-88-4 methyl iodide 
• 635702-59-9 3-methyl-6-nitro-1H-indazole sulfate 
• 578-54-1 ortho-ethylaniline 
• 20191-74-6 2-ethyl-5-nitroaniline 
• 444731-73-1 2,3?dimethyl?6?nitro?2H?indazole 

Downstream Products

• 1376676-65-1 N,2,3-trimethyl-2H-indazole-6-amine 
• 444731-75-3 N-(2-chloropyrimidin-4-yl)-N-methyl-2,3-dimethyl-2H-indazole-6-amine 
• 444731-52-6 pazopanib 
• 1620059-34-8 C₁₆H₁₆ClN₅ 
• 1620059-11-1 5-[[4-[N-(2,3-dimethyl-2H-indazol-6-yl)-N-methylamino]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl]amino]-2-methyl-benzenesulfonamide 
• 1620843-77-7 5-[[4-[(2,3-dimethyl-2H-indazol-6-yl)amino]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl]amino]-2-methyl-benzenesulfonamide 
• 1620059-12-2 3-[[4-[N-(2,3-dimethyl-2H-indazol-6-yl)-N-methylamino]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl]amino]-benzenesulfonamide 
• 1620843-78-8 3-[[4-[(2,3-dimethyl-2H-indazol-6-yl)amino]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl]amino]-benzenesulfonamide 
• 1620843-79-9 3-[[4-[N-(2,3-dimethyl-2H-indazol-6-yl)-N-methylamino]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl]amino]-4-methoxy-benzenesulfonamide 
• 1620059-14-4 N²-(3,4-dimethoxyphenyl)-N⁴-(2,3-dimethyl-2H-indazol-6-yl)-N⁴-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diamine 
• 1620059-15-5 N²-(3-bromohenyl)-N⁴-(2,3-dimethyl-2H-indazol-6-yl)-N⁴-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diamine 
• 1620059-16-6 N⁴-(2,3-dimethyl-2H-indazol-6-yl)-N²-(3-fluorohenyl)-N⁴-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diamine 
• 1620843-80-2 5-[[4-[N-(2,3-dimethyl-2H-indazol-6-yl)-N-methylamino]-5,6,7,8-tetrahydroquinazolin-2-yl]amino]-2-methyl-benzenesulfonamide 
• 1620843-82-4 5-[[4-[(2,3-dimethyl-2H-indazol-6-yl)amino]-5,6,7,8-tetrahydroquinazolin-2-yl]amino]-2-methyl-benzenesulfonamide 

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.

Design, synthesis and bioevaluation of novel 6-substituted aminoindazole derivatives as anticancer agents

In the present study, a series of 6-substituted aminoindazole derivatives were designed, synthesized, and evaluated for bio-activities. The compounds were initially designed as indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors based on the structural feature of five IDO1 inhibitors, which are currently on clinical trials, and the important anticancer activity of the indazole scaffold. One of them, compound N-(4-fluorobenzyl)-1,3-dimethyl-1H-indazol-6-amine (36), exhibited a potent anti-proliferative activity with an IC50 value of 0.4 ± 0.3 μM in human colorectal cancer cells (HCT116). This compound also remarkably suppressed the IDO1 protein expression. In the cell-cycle studies, the suppressive activity of compound 36 in HCT116 cells was related to the G2/M cell cycle arrest. Altogether, the current findings demonstrate that compound 36 would be promising for further development as a potential anticancer agent.

Hydrochloric acid [...] of the method for the preparation of intermediates

The invention discloses a preparation method of an intermediate (2,3-dimethyl-N-(2-chloropyrimidine-4-base)-N-methyl-2H-indazole-6-amine) of pazopanib hydrochloride as shown in a formula I. The preparation method comprises the step of performing nucleophilic substitution reaction on a compound III and 2,4-dichloropyrimidine in an organic solvent under the action of alkali, wherein the reaction temperature is 0-160 DEG C. According to the preparation method disclosed by the invention, raw materials are low in price and easy to obtain, and the preparation method is convenient to operate, high in product yield and suitable for industrial large-scale production.