705263-10-1

Basic information

• Product Name: 6-BROMO-PYRAZOLO[1,5-A]PYRIMIDINE
• Synonyms: 6-BROMO-PYRAZOLO[1,5-A]PYRIMIDINE;6-Bromopyrazolo[1,5-a]pyr...;6-broMopyrazolo[1;Pyrazolo[1,5-a]pyriMidine, 6-broMo-
• CAS NO: 705263-10-1
• Molecular Formula: C₆H₄BrN₃
• Molecular Weight: 198.02006
• Product Categories: Heterocycle-Pyrimidine series
• Mol File: 705263-10-1.mol

Chemical Properties

• Melting Point: 122-124℃
• Appearance: /
• Density: 1.891g/cm3
• Refractive Index: 1.751
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -0.81±0.30(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Light Sensitive
• CAS DataBase Reference: 6-BROMO-PYRAZOLO[1,5-A]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-PYRAZOLO[1,5-A]PYRIMIDINE(705263-10-1)
• EPA Substance Registry System: 6-BROMO-PYRAZOLO[1,5-A]PYRIMIDINE(705263-10-1)

Safety Data

• Hazardous Substances Data: 705263-10-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-BROMO-PYRAZOLO[1,5-A]PYRIMIDINE is used as a reactant in the synthesis of LDN-212854, a selective and potent inhibitor of the BMP type I receptor kinases. 6-BROMO-PYRAZOLO[1,5-A]PYRIMIDINE plays a crucial role in the development of treatments for various diseases and conditions, particularly those related to the regulation of bone and tissue growth.
In the synthesis of LDN-212854, 6-BROMO-PYRAZOLO[1,5-A]PYRIMIDINE contributes to the formation of the final product, which has the potential to modulate the activity of BMP type I receptor kinases. This modulation can lead to the regulation of cellular processes and the treatment of diseases associated with abnormal BMP signaling. The use of 6-BROMO-PYRAZOLO[1,5-A]PYRIMIDINE in this context highlights its importance in the pharmaceutical industry and its potential applications in drug discovery and development.

InChI:InChI=1/C6H4BrN3/c7-5-3-8-6-1-2-9-10(6)4-5/h1-4H

Upstream product

• 1820-80-0 3-aminopyrazole 
• 20591-60-0 (2Z)-2-bromo-3-(dimethylamino)prop-2-enal 
• 2065-75-0 2-Bromo-malonaldehyde 
• 1225387-53-0 3⁽⁵⁾-aminopyrazole 

Downstream Products

• 1109284-33-4 6-bromo-3-iodopyrazolo[1,5-a]pyrimidine 
• 1062368-26-6 tert-butyl 4-(4-(3-bromopyrazolo[1,5-a]pyrimidin-6-yl)phenyl)piperazine-1-carboxylate 
• 1416437-27-8 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyrimidine 
• 1580489-59-3 pyrazolo[1,5-a]pyrimidin-6-ol 
• 1581682-29-2 4-((1R,4R,5R)-5-amino-2-azabicyclo[2.2.1]heptan-2-yl)-6-fluoro-N-methyl-2-(pyrazolo[1,5-a]pyrimidin-6-yloxy)-9H-pyrimido[4,5-b]indol-8-amine trifluoroacetate 
• 1581684-22-1 tert-butyl (6-fluoro-2,4-bis(pyrazolo[1,5-a]pyrimidin-6-yloxy)-9H-pyrimido[4,5-b]indol-8-yl)(methyl)carbamate 
• 1581682-27-0 tert-butyl (4-((1R,4R,5R)-5-((tert-butoxycarbonyl)amino)-2-azabicyclo[2.2.1]heptan-2-yl)-6-fluoro-2-(pyrazolo[1,5-a]pyrimidin-6-yloxy)-9H-pyrimido[4,5-b]indol-8-yl)(methyl)carbamate 
• 1435615-02-3 6-(4-(4-methylpiperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrimidine 
• 1435615-34-1 C₂₂H₂₀N₄O 
• 1435615-06-7 4-(4-(3-iodopyrazolo[1,5-a]pyrimidin-6-yl)phenyl)morpholine 
• 1435615-14-7 C₁₇H₁₈IN₅ 
• 1435615-10-3 C₁₆H₁₆IN₅ 

Relevant articles and documents

SUBSTITUTED FUSED AROMATIC RING DERIVATIVE, COMPOSITION AND USE THEREOF

Provided are a substituted fused aromatic ring derivative, a composition containing the compound, and a use thereof. The substituted fused aromatic ring derivative is a compound represented by formula (I) or a tautomer, stereoisomer, prodrug, crystal form, pharmaceutically acceptable salt, hydrate or solvate thereof. The compound and the composition can be used to treat various protein tyrosine kinase-mediated diseases or disorders.

NITROGENOUS HETEROCYCLIC COMPOUND, PREPARATION METHOD, INTERMEDIATE, COMPOSITION, AND APPLICATION

A nitrogenous heterocyclic compound, a preparation method, an intermediate, a composition, and an application. The present invention provides a nitrogenous heterocyclic compound as represented by formula I, pharmaceutically acceptable salts thereof, enantiomers thereof, diastereoisomers thereof, tautomers thereof, solvates thereof, metabolites thereof, or prodrugs thereof. The compound has high inhibitory activity against ErbB2 tyrosine kinase, has good inhibitory activity against human breast cancer cells BT-474, human gastric cancer cells NCI-N87 and the like with high expression of ErbB2, and in addition has relatively weak inhibitory activity against EGFR kinase, that is, the compound is an EGFR/ErbB2 double target inhibitor that attenuates EGFR kinase inhibitory activity or a small-molecule inhibitor having selectivity for an ErbB2 target. (I)

Synthetic method for 3-bromopyrazolo[1,5-alpha]pyrimidine-6-formic acid

The invention provides a synthetic method for 3-bromopyrazolo[1,5-alpha]pyrimidine-6-formic acid. The synthetic method comprises the following steps: 3-amino-1H-pyrazole is used as a raw material, the3-amino-1H-pyrazole and 2-bromomalonaldehyde are subjected to condensation to obtain 6-bromo-pyrazolo[1,5-alpha]pyrimidine, the 6-bromo-pyrazolo[1,5-alpha]pyrimidine reacts with PdCl2 and triethylamine to obtain methyl pyrazolo[1,5-alpha]pyrimidine-6-formate, a hydrolysis reaction is performed to obtain pyrazolo[1,5-alpha]pyrimidine-6-formic acid, and finally the pyrazolo[1,5-alpha]pyrimidine-6-formic acid reacts with N-bromosuccinimide to obtain the 3-bromopyrazolo[1,5-alpha]pyrimidine-6-formic acid. The synthetic method for the 3-bromopyrazolo[1,5-alpha]pyrimidine-6-formic acid provided bythe invention has a simple synthetic route, a reasonable process and low costs of the raw materials, is simple, easy to obtain and convenient for operation and post treatment, has a high total yield,does not use a highly-toxic reagent, is easy to amplify, and can be used for large-scale production of the 3-bromopyrazolo[1,5-alpha]pyrimidine-6-formic acid.

A synthetic bone morphogenetic protein receptor inhibitors

The invention discloses a method for synthesizing a bone morphogenetic protein receptor inhibitor, and solves the problem of long inhibitor synthesis route in the prior art. The method comprises the following steps: 1, obtaining an intermediate represented by formula (III) shown in the specification, wherein R1 in the formula (III) can be a first formula or a second formula also shown in the specification; 2, adding 5-bromoquinoline to the intermediate represented by formula (III), adding potassium acetate and palladium acetate, adding N,N-dimethyl acetamide, reacting, and cooling to room temperature; and 3, adding water to precipitate a solid when the R1 is the first formula, drying, and separating to obtain a product 1; and extracting the above obtained reaction solution by ethyl acetate when the R1 is the second formula, drying the obtained organic phase to remove a solvent, separating to obtain the product 1, dissolving the product 1 in methanol, adding concentrated hydrochloric acid, reacting to precipitate a solid, carrying out pumping filtration, washing, and drying to obtain a product 2. The method has the advantages of short preparation steps, low price of adopted raw materials, and high yield of target products.

Design, synthesis, and biological activity of 4-(imidazo[1,2-b]pyridazin-3-yl)-1H-pyrazol-1-yl-phenylbenzamide derivatives as BCR–ABL kinase inhibitors

A series of 4-((pyrazolo[1,5-a]pyrimidin-6-yl)-1H-pyrazol-1-yl)phenyl-3-benzamide derivatives and 4-((imidazo[1,2-b]pyridazin-3-yl)-1H-pyrazol-1-yl-)phenyl-3-benzamide derivatives were designed, synthesized as new BCR–ABL tyrosine kinase inhibitors by using combinational strategies of scaffold hopping and conformational constraint. These new compounds were screened for BCR–ABL1 kinase inhibitory activity, and most of them appeared good inhibitory activity against BCR–ABL1 kinase. One of the most potent compounds 16a strongly suppressed BCR–ABL1 kinase with IC50value of 8.5 nM. The tested compounds 16a and 16i showed strong inhibitory activities against K562 with IC50value of less than 2 nM. Molecular docking studies indicated that these compounds fitted well with the active site of BCR–ABL1 protein. The results showed these inhibitors may serve as lead compounds for further developing new drugs targeted BCR–ABL kinase.

BMP INHIBITORS AND METHODS OF USE THEREOF

The present invention provides small molecule inhibitors of BMP signaling. These compounds may be used to modulate cell growth, differentiation, proliferation, and apoptosis, and thus may be useful for treating diseases or conditions associated with BMP signaling, including inflammation, cardiovascular disease, hematological disease, cancer, and bone disorders, as well as for modulating cellular differentiation and/or proliferation. These compounds may also be used to reduce circulating levels of ApoB-100 or LDL and treat or prevent acquired or congenital hypercholesterolemia or hyperlipoproteinemia; diseases, disorders, or syndromes associated with defects in lipid absorption or metabolism; or diseases, disorders, or syndromes caused by hyperlipidemia.

Synthesis and structure-activity relationships of a novel and selective bone morphogenetic protein receptor (BMP) inhibitor derived from the pyrazolo[1.5-a]pyrimidine scaffold of Dorsomorphin: The discovery of ML347 as an ALK2 versus ALK3 selective MLPCN probe

A structure-activity relationship of the 3- and 6-positions of the pyrazolo[1,5-a]pyrimidine scaffold of the known BMP inhibitors dorsomorphin, 1, LDN-193189, 2, and DMH1, 3, led to the identification of a potent and selective compound for ALK2 versus ALK3. The potency contributions of several 3-position substituents were evaluated with subtle structural changes leading to significant changes in potency. From these studies, a novel 5-quinoline molecule was identified and designated an MLPCN probe molecule, ML347, which shows >300-fold selectivity for ALK2 and presents the community with a selective molecular probe for further biological evaluation.

METABOTROPIC GLUTAMATE RECEPTOR MODULATORS

The invention relates to heterocyclic derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are mGluR5 modulators and are therefore useful for the control and prevention of acute and/or chronic neurological disorders

PYRAZOLO[1,5-A]PYRIMIDINE DERIVATIVES

Compounds of the following formula (I) are inhibitors of microtubule affinity regulating kinase, and hence find use in the treatment of neurodegenerative diseases associated with hyperphosphorylation of tau.

INHIBITORS OF THE BMP SIGNALING PATHWAY

The present invention provides small molecule inhibitors of BMP signaling. These compounds may be used to modulate cell growth, differentiation, proliferation, and apoptosis, and thus may be useful for treating diseases or conditions associated with BMP signaling, including inflammation, cardiovascular disease, hematological disease, cancer, and bone disorders, as well as for modulating cellular differentiation and/or proliferation.