61272-71-7

Basic information

• Product Name: 5-BROMO-1H-INDAZOL-3-AMINE
• Synonyms: 5-BROMO-1H-INDAZOL-3-AMINE;5-BROMO-1H-INDAZOL-3-YLAMINE;5-Bromo-1H-indazol-3-amine 95%;5-bromo-1H-indazol-3-amine (en);3-Amino-5-bromo-1H-indazole;3-Amino-5-bromoindazole;3-Amino-5-bromo-1H-indazole 95%;5-bromo-1H-indazol-3-amine(SALTDATA: FREE)
• CAS NO: 61272-71-7
• Molecular Formula: C₇H₆BrN₃
• Molecular Weight: 212.05
• Product Categories: Amines;Fused Ring Systems
• Mol File: 61272-71-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 171-175
• Boiling Point: 431.3 °C at 760 mmHg
• Flash Point: 214.7 °C
• Appearance: Clear colorless/Liquid
• Density: 1.867g/cm³
• Vapor Pressure: 1.21E-07mmHg at 25°C
• Refractive Index: 1.8
• Storage Temp.: Room temperature.
• PKA: 13?+-.0.40(Predicted)
• CAS DataBase Reference: 5-BROMO-1H-INDAZOL-3-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-1H-INDAZOL-3-AMINE(61272-71-7)
• EPA Substance Registry System: 5-BROMO-1H-INDAZOL-3-AMINE(61272-71-7)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25-36/37/38-22
• Safety Statements: 45-36/37/39-26-22
• HazardClass: IRRITANT
• Hazardous Substances Data: 61272-71-7(Hazardous Substances Data)

Usage

Uses

5-BROMO-1H-INDAZOL-3-AMINE can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Synthesis

Hydrazine hydrate (18 mL) was added to Example 62C (1.93 g, 6.94 mmol.) in ethanol (10 mL). The mixture was heated to 95°C. overnight. The mixture was diluted with ethyl acetate and washed with water. Some of the product precipitated in the separatory funnel and was filtered to afford the title compound. The ethyl acetate layer was concentrated under reduced pressure and the resulting solid was triturated with methanol. 5-bromo-1H-indazol-3-amine. The title compound was prepared according to the procedure outlined in Example 62D substituting 5-bromo-2-fluorobenzonitrile for Example 62C. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.55 (s, 1H), 7.92 (d, J=1.87 Hz, 1H), 7.30 (dd, J=8.79, 1.89 Hz, 1H), 7.19 (d, J=8.78 Hz, 1H), 5.41 (s, 2H).

InChI:InChI=1/C7H6BrN3/c8-4-1-2-6-5(3-4)7(9)11-10-6/h1-3H,(H3,9,10,11)

Upstream product

• 39263-32-6 2-amino-5-bromobenzonitrile 
• 179897-89-3 5-Bromo-2-fluoro-benzonitrile 

Downstream Products

• 1093965-09-3 5-(1-methyl-1H-pyrazol-4-yl)-1H-indazol-3-amine 
• 1036380-75-2 3-amino-5-bromobenzo[b]thiophene-2-carboxylic acid methyl ester 
• 1432912-73-6 tert-butyl 3-[bis(tert-butoxycarbonyl)amino]-5-(5-chloro-2-{4-[(2,4-dimethoxybenzyl)-(1,2,4-thiadiazol-5-yl)sulfamoyl]-2,5-difluorophenoxy}phenyl)-1H-indazole-1-carboxylate 
• 1432912-66-7 tert-butyl 3-[bis(tert-butoxycarbonyl)amino]-5-(5-chloro-2-hydroxyphenyl)-1H-indazole-1-carboxylate 

Relevant articles and documents

SMALL MOLECULE INHIBITORS OF NF-kB INDUCING KINASE

The present invention relates to compounds that inhibit NIK and pharmaceutical compositions comprising such compounds and methods of using the same. These compounds and pharmaceutical compositions are envisaged to be useful for preventing or treating diseases such as cancer (such as B-cell malignancies including leukemias, lymphomas and myeloma), inflammatory disorders, autoimmune disorders, immunodermatologic disorders such as palmoplantar pustulosis and hidradenitis suppurativa, and metabolic disorders such as obesity and diabetes.

Fragment-based discovery of JAK-2 inhibitors

Fragment-based hit identification coupled with crystallographically enabled structure-based drug design was used to design potent inhibitors of JAK-2. After two iterations from fragment 1, we were able to increase potency by greater than 500-fold to provide sulfonamide 13, a 78-nM JAK-2 inhibitor.

6-AMINOIMIDAZO[1,2-b]PYRIDAZINE ANALOGS AS RHO KINASE INHIBITORS FOR THE TREATMENT OF RHO KINASE-MEDIATED DISEASES AND CONDITIONS

Methods for using 6-aminoimidazo[1,2-b]pyridazine analogs are disclosed herein to treat rho kinase-mediated diseases or rho kinase-mediated conditions, including controlling intraocular pressure and treating glaucoma, are disclosed. Ophthalmic pharmaceutical compositions useful in the treatment of eye diseases such as glaucoma, and additionally useful for controlling intraocular pressure, the compositions comprising an effective amount of 6-aminoimidazo[1,2-b]pyridazine analogs, are disclosed herein.