316810-86-3

Basic information

• Product Name: 7-AMino-5-broMo-1H-indazo...
• Synonyms: 7-AMino-5-broMo-1H-indazo...;7-AMino-5-broMo-1H-indazole;1H-Indazol-7-aMine,5-broMo-;Indazol-7-amine, 5-bromo-;7-amino-5-bromoindazole;5-bromo-1H-indazol-7-amine
• CAS NO: 316810-86-3
• Molecular Formula: C₇H₆BrN₃
• Molecular Weight: 212.05
• Mol File: 316810-86-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 426.5±25.0 °C(Predicted)
• Appearance: /
• Density: 1.867±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 13?+-.0.40(Predicted)
• CAS DataBase Reference: 7-AMino-5-broMo-1H-indazo...(CAS DataBase Reference)
• NIST Chemistry Reference: 7-AMino-5-broMo-1H-indazo...(316810-86-3)
• EPA Substance Registry System: 7-AMino-5-broMo-1H-indazo...(316810-86-3)

Safety Data

• Hazardous Substances Data: 316810-86-3(Hazardous Substances Data)

Usage

General Description

The chemical 7-Amino-5-Bromine-1H-Indazole is a white to light yellow powder that is primarily used as a starting material in the synthesis of pharmaceutical compounds. It is a heterocyclic compound containing an indazole ring, which has been found to exhibit various biological activities. This chemical is also being investigated for its potential applications in the field of medicinal chemistry as a potential drug candidate for the treatment of various diseases, including cancer and neurological disorders. 7-Amino-5-Bromine-1H-Indazole is a valuable building block for the production of diverse chemical compounds and is of significant interest to researchers in the pharmaceutical industry.

Synthetic route

5-bromo-7-nitro-1H-indazole (316810-82-9) → 5-bromo-1H-indazol-7-amine (316810-86-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol Catalytic hydrogenation;	85%
With iron In ethanol; water at 80℃; for 4h;	50.5%
With iron; ammonium chloride In ethanol; water at 80℃; for 4h;	50.5%
With iron; ammonium chloride In ethanol; water at 80℃; for 4h;	50.5%

2-Methyl-6-nitroaniline (570-24-1) → 5-bromo-1H-indazol-7-amine (316810-86-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 60 percent / N-bromosuccinimide / CCl4 2: 64 percent / NaNO2; AcOH 3: 85 percent / H2 / Pd/C / ethanol View Scheme

4-bromo-2-methyl-6-nitroaniline (77811-44-0) → 5-bromo-1H-indazol-7-amine (316810-86-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / NaNO2; AcOH 2: 85 percent / H2 / Pd/C / ethanol View Scheme
Multi-step reaction with 2 steps 1: acetic acid; sodium nitrite / water / 6 h / 0 - 20 °C 2: iron / water; ethanol / 4 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: acetic acid; sodium nitrite / water / 6 h / 20 °C 2: iron; ammonium chloride / water; ethanol / 4 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: acetic acid; sodium nitrite / water / 6 h / 0 - 20 °C 2: iron; ammonium chloride / water; ethanol / 4 h / 80 °C View Scheme

Cyclohexyloxirane (3483-39-4) + 5-bromo-1H-indazol-7-amine (316810-86-3) → C15H20BrN3O + C15H20BrN3O

Conditions	Yield
With sodium hydroxide In ethanol; water at 110℃; for 3h; pH=10-11;	A 45% B 40%

ethyl acetoacetate (141-97-9) + 5-bromo-1H-indazol-7-amine (316810-86-3) → 7H-9-bromo-4-methylpyrazolo[1,5,4-ef][1,5]benzodiazepin-6-one + 5H-9-bromo-6-methylpyrazolo[1,5,4-ef][1,5]benzodiazepin-4-one

Conditions	Yield
In xylene for 5h; cyclocondensation; Heating;	A 39% B 40%

formaldehyd (50-00-0) + 5-bromo-1H-indazol-7-amine (316810-86-3) → C9H10BrN3

Conditions	Yield
Stage #1: formaldehyd; 5-bromo-1H-indazol-7-amine In methanol for 0.5h; Stage #2: With methanol; sodium cyanoborohydride for 0.166667h; Stage #3: With trifluoroacetic acid In methanol for 16h;	22.7%

Upstream product

• 77811-44-0 4-bromo-2-methyl-6-nitroaniline 
• 570-24-1 2-Methyl-6-nitroaniline 
• 316810-82-9 5-bromo-7-nitro-1H-indazole 

Relevant articles and documents

X-ray Structure-Guided Discovery of a Potent, Orally Bioavailable, Dual Human Indoleamine/Tryptophan 2,3-Dioxygenase (hIDO/hTDO) Inhibitor That Shows Activity in a Mouse Model of Parkinson’s Disease

Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan 2,3-dioxygenase (hTDO) have been closely linked to the pathogenesis of Parkinson’s disease (PD); nevertheless, development of dual hIDO1 and hTDO inhibitors to evaluate their potential efficacy against PD is still lacking. Here, we report biochemical, biophysical, and computational analyses revealing that 1H-indazole-4-amines inhibit both hIDO1 and hTDO by a mechanism involving direct coordination with the heme ferrous and ferric states. Crystal structure-guided optimization led to23, which manifested IC50values of 0.64 and 0.04 μM to hIDO1 and hTDO, respectively, and had good pharmacokinetic properties and brain penetration in mice.23showed efficacy against the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse motor coordination deficits, comparable to Madopar, an anti-PD medicine. Further studies revealed that different from Madopar,23likely has specific anti-PD mechanisms involving lowering IDO1 expression, alleviating dopaminergic neurodegeneration, reducing inflammatory cytokines and quinolinic acid in mouse brain, and increasing kynurenic acid in mouse blood.

Indazole compounds containing nitrogen substituents, and application of same as IDO inhibitors

The invention discloses nitrogen substituent-containing indazole compounds as shown in a formula (I) which is described in the specification, a preparation method for the compounds, and application ofthe compounds as IDO inhibitors. The compounds provided by the invention can be used for preventing and/or treating a plurality of diseases, such as Alzheimer's disease, cataract, infections relatedto cellular immune activation, autoimmune diseases, AIDS, cancers, depression, the metabolic disorder of tryptophan or the like.

Research in 7-aminoindazole series: Synthesis of new halo-7H-4-methylpyrazolo[1,5,4-ef][1,5]benzodiazepin-6-ones and 5H-9-halo-6-methylpyrazolo[1,5,4-ef][1,5]benzodiazepin-4-ones

A new class of 7-aminohaloindazoles has been synthesized. Reactivity of the amino groups of these bicyclic systems has been investigated. The halogenated pyrazolo-1,5-benzodiazepinones have been synthesized by the condensation of 7-aminoindazoles with ethyl acetoacetate.