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

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

Used in Pharmaceutical Industry:
2,3-DIMETHYL-2H-INDAZOL-6-AMINE is used as an impurity in the synthesis of Pazopanib (P210925) hydrochloride for its role in targeting VEGFR and PDGFR. This application is significant because Pazopanib hydrochloride is an oral angiogenesis inhibitor, which means it helps prevent the growth of new blood vessels that supply nutrients to tumors, thereby inhibiting their growth and progression.

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

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

Downstream Products

• 444731-74-2 N-(2-chloropyrimidin-4-yl)-2,3-dimethyl-2H-indazol-6-amine 
• 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 
• 1572439-40-7 N-carbamimidoyl-4-((4-((2,3-dimethyl-2H-indazol-6-yl)amino)pyrimidin-2-yl)amino)benzenesulfonamide 
• 1572439-47-4 N⁴-(2,3-dimethyl-2H-indazol-6-yl)-N²-(4-fluorophenyl)pyrimidine-2,4-diamine 
• 1572439-04-3 4-((4-((2,3-dimethyl-2H-indazol-6-yl)(methyl)amino)pyrimidin-2-yl)amino)benzenesulfonamide 
• 1572439-13-4 4-((4-((2,3-dimethyl-2H-indazol-6-yl)(methyl)amino)pyrimidin-2-yl)amino)-N-(pyrimidin-2-yl)benzenesulfonamide 
• 1572439-21-4 4-((4-((2,3-dimethyl-2H-indazol-6-yl)(methyl)amino)pyrimidin-2-yl)amino)-N-(4-methylpyrimidin-2-yl)benzenesulfonamide 
• 1572439-28-1 4-((4-((2,3-dimethyl-2H-indazol-6-yl)(methyl)amino)pyrimidin-2-yl)amino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide 
• 1572439-36-1 4-((4-((2,3-dimethyl-2H-indazol-6-yl)(methyl)amino)pyrimidin-2-yl)amino)-N-(5-methylisoxazol-3-yl)benzenesulfonamide 
• 1572439-44-1 N-carbamimidoyl-4-((4-((2,3-dimethyl-2H-indazol-6-yl)(methyl)amino)pyrimidin-2-yl)amino)benzenesulfonamide 
• 1572439-50-9 N²-benzyl-N⁴-(2,3-dimethyl-2H-indazol-6-yl)pyrimidine-2,4-diamine 
• 1572439-53-2 N⁴-(2,3-dimethyl-2H-indazol-6-yl)-N²-(4-fluorobenzyl)pyrimidine-2,4-diamine 

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.

High Turnover Pd/C Catalyst for Nitro Group Reductions in Water. One-Pot Sequences and Syntheses of Pharmaceutical Intermediates

Commercially available Pd/C can be used as a catalyst for nitro group reductions with only 0.4 mol % Pd loading. The reaction can be performed using either silane as a transfer hydrogenating agent or simply a hydrogen balloon (μ1 atm pressure). With this technology, a series of nitro compounds was reduced to the desired amines in high chemical yields. Both the catalyst and surfactant were recycled several times without loss of reactivity.

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.

Method for synthesizing 2,3-dimethyl-6-amino-2H-indazole by microchannel hydrogenation

The invention discloses a method for synthesizing 2,3-dimethyl-6-amino-2H-indazole by microchannel hydrogenation, and belongs to the technical field of synthesis of pharmaceutical intermediates. The method comprises steps as follows: firstly, raw material 2,3-dimethyl-6-nitro-2H-indazole and a catalyst Pd/C are added to a solvent, a gel solution is prepared, the gel solution and hydrogen are fed into a microchannel reactor under the condition of certain pressure and temperature, and 2,3-dimethyl-6-amino-2H-indazole is synthesized by hydrogenation in a short time of tens of seconds to a few minutes. The method integrates the characteristics that a microchannel has efficient mass and heat transfer capabilities and is easy to amplify directly, the degree of hydrogenation can reach 99.5%, andproduct yield is higher than 98%. The method has higher operational safety and selectivity, can realize continuous production of reaction and has the advantages of low energy consumption, short reaction time, high safety, simple technological process, low production cost, no side reaction and the like.

2,3-dimethyl-6-urea -2H-indazoles and its preparation method and application

The invention discloses a 2, 3-dimethyl-6-urea-2H-indazole compound shown by the following general formula (I), medicinal salt or a solvent compound thereof, wherein Ar is substituted or unsubstituted phenyl or aromatic matrix. The invention also discloses a preparation method and application of the compound. The compound can regulate signal transduction of tyrosine kinase, inhibit bad cellular proliferation, and particularly has obvious curative effect for tumors.

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.

PROCESS FOR THE PREPARATION OF PAZOPANIB OR SALTS THEREOF

The present invention provides a process for the preparation of pazopanib of Formula Ia or salts, and intermediates thereof.

Discovery and synthesis of N2,N4-substitued- cycloalkyl[d]pyrimidine-2,4-diamine analogs: The first examples of small-molecular FGFR-1 activator

A series of novel, cycloalkyl-modified pazopanib analogs 2 and 3 were designed and synthesized. Their kinase modulatory effects on FGFR-1, VEGFR-2, PDGFR-β, and c-KIT were evaluated by the caliper mobility shift assay. Introduction of cycloalkyl into the pyrimidine linker of pazopanib almost abolished the four kinases inhibitory potency of compounds 2 and 3, but surprisingly, resulted in good activation effects on FGFR-1. Compounds 3d and 3g showed double-digit, nanomolar, selective activation effects on FGFR-1, and could be classified as first-generation small molecular activators of FGFR-1 kinase.

Synthesis and biological evaluation of novel pazopanib derivatives as antitumor agents

A series of novel pazopanib derivatives, 7a-m, were designed and synthesized by modification of terminal benzene and indazole rings in pazopanib. The structures of all the synthesized compounds were confirmed by 1H NMR and MS. Their inhibitory

A novel practical synthesis of pazopanib: An anticancer drug

Abstract: This paper reports a novel approach to synthesize pazopanib. In our synthetic route, the potently mutagenic alkylating agents such as dimethyl sulfate and methyl iodide are avoided. A novel regioselective methylation of the 2- position of 3-methyl-6-nitro-1H-indazole was reported. This novel route is one step shorter than the previously reported route.