374930-88-8

Basic information

• Product Name: 5-BROMO-2-(4-BOC-PIPERAZIN-1-YL)PYRIMIDINE
• Synonyms: 5-BROMO-2-(4-BOC-PIPERAZIN-1-YL)PYRIMIDINE;4-(5-BROMOPYRIMIDIN-2-YL)PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;4-(5-BROMOPYRIMIDIN-2-YL)PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER, 95+%;5-Bromo-2-[(N-Boc)piperazin-1-yl]pyrimidine;1-Boc-4-(5-bromopyrimidin-2-yl)piperazine;1-Piperazinecarboxylic acid, 4-(5-bromo-2-pyrimidinyl)-, 1,1-dimethylethyl ester;1-N-Boc-4-(5-broMopyriMidin-2-yl)piperazine;4-(5-bromo-2-pyrimidinyl)-1-piperazinecarboxylic acid tert-butyl ester
• CAS NO: 374930-88-8
• Molecular Formula: C₁₃H₁₉BrN₄O₂
• Molecular Weight: 343.22
• Product Categories: pharmacetical;Organohalides;Pyrimidine
• Mol File: 374930-88-8.mol

Chemical Properties

• Boiling Point: 451°Cat760mmHg
• Flash Point: 226.5°C
• Appearance: /
• Density: 1.414g/cm³
• Vapor Pressure: 2.53E-08mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: 2-8°C(protect from light)
• PKA: 3.46±0.42(Predicted)
• CAS DataBase Reference: 5-BROMO-2-(4-BOC-PIPERAZIN-1-YL)PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2-(4-BOC-PIPERAZIN-1-YL)PYRIMIDINE(374930-88-8)
• EPA Substance Registry System: 5-BROMO-2-(4-BOC-PIPERAZIN-1-YL)PYRIMIDINE(374930-88-8)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• Hazardous Substances Data: 374930-88-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H19BrN4O2/c1-13(2,3)20-12(19)18-6-4-17(5-7-18)11-15-8-10(14)9-16-11/h8-9H,4-7H2,1-3H3

Upstream product

• 32779-37-6 2,5-dibromopyrimidine 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 32779-36-5 5-Bromo-2-chloropyrimidine 

Downstream Products

• 603965-77-1 ethyl 2-(piperazin-1-yl) pyrimidine-5-carboxylate 
• 940284-98-0 tert-butyl 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]piperazine-1-carboxylate 
• 1241896-42-3 {5-[2-(4-{[2-(trifluoromethyl)phenyl]carbonyl}piperazin-1-yl)pyrimidin-5-yl]-2H-tetrazol-2-yl}acetic acid 
• 1241898-51-0 ethyl {5-[2-(4-{[2-(trifluoromethyl)phenyl]carbonyl}piperazin-1-yl)pyrimidin-5-yl]-2H-tetrazol-2-yl}acetate 
• 1310685-48-3 D-750776 
• 1310685-56-3 (4-(5-benzylpyrimidin-2-yl)piperazin-1-yl)(4-((2-phenylquinazolin-4-ylamino)methyl)phenyl)methanone 
• 1310685-55-2 (4-(5-benzylpyrimidin-2-yl)piperazin-1-yl)(4-(2-phenylquinazolin-4-ylamino)phenyl)methanone 
• 1310685-54-1 (4-(5-benzylpyrimidin-2-yl)piperazin-1-yl)(3-(2-phenylquinazolin-4-ylamino)phenyl)methanone 
• 1310685-50-7 (4-(5-benzylpyrimidin-2-yl)piperazin-1-yl)(4-((quinazolin-4-ylamino)methyl)phenyl)methanone 
• 1310685-49-4 (4-(5-benzylpyrimidin-2-yl)piperazin-1-yl)(4-(quinazolin-4-ylamino)phenyl)methanone 
• 1310685-42-7 4-(4-(5-benzylpyrimidin-2-yl)piperazin-1-yl)-2-phenylquinazoline 
• 1310685-40-5 D-750901 
• 1283119-60-7 tert-butyl 4-(5-benzylpyrimidin-2-yl)piperazine-1-carboxylate 
• 1283119-10-7 5-benzyl-2-(piperazin-1-yl)pyrimidine 

Relevant articles and documents

Synthesis and biological evaluation of disubstituted pyrimidines as selective 5-HT2C agonists

Here, we describe the synthesis of disubstituted pyrimidine derivatives and their biological evaluation as selective 5-HT2C agonists. To improve selectivity for 5-HT2C over other subtypes, we synthesized two series of disubstituted pyrimidines with fluorophenylalkoxy groups at either the 5-position or 4-position and varying cyclic amines at the 2-position. The in vitro cell-based assay and binding assay identified compounds 10a and 10f as potent 5-HT2C agonists. Further studies on selectivity to 5-HT subtypes and drug-like properties indicated that 2,4-disubstituted pyrimidine 10a showed a highly agonistic effect on the 5-HT2C receptor, with excellent selectivity, as well as exceptional drug-like properties, including high plasma and microsomal stability, along with low CYP inhibition. Thus, pyrimidine 10a could be considered a viable lead compound as a 5-HT2C selective agonist.

Improvement of Aqueous Solubility of Lapatinib-Derived Analogues: Identification of a Quinolinimine Lead for Human African Trypanosomiasis Drug Development

Lapatinib, an approved epidermal growth factor receptor inhibitor, was explored as a starting point for the synthesis of new hits against Trypanosoma brucei, the causative agent of human African trypanosomiasis (HAT). Previous work culminated in 1 (NEU-1953), which was part of a series typically associated with poor aqueous solubility. In this report, we present various medicinal chemistry strategies that were used to increase the aqueous solubility and improve the physicochemical profile without sacrificing antitrypanosomal potency. To rank trypanocidal hits, a new assay (summarized in a cytocidal effective concentration (CEC50)) was established, as part of the lead selection process. Increasing the sp3 carbon content of 1 resulted in 10e (0.19 μM EC50 against T. brucei and 990 μM aqueous solubility). Further chemical exploration of 10e yielded 22a, a trypanocidal quinolinimine (EC50: 0.013 μM; aqueous solubility: 880 μM; and CEC50: 0.18 μM). Compound 22a reduced parasitemia 109 fold in trypanosome-infected mice; it is an advanced lead for HAT drug development.

POLY-ADP RIBOSE POLYMERASE (PARP) INHIBITORS

The present invention is related to a pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and a compound represented by the following structural formula: The present invention is also related a method of treating a subject with a disease which can be ameliorated by inhibition of poly(ADP-ribose)polymerase (PARP). The definitions of the variables are provided herein.

GLYCOSIDASE INHIBITORS

Compounds of formula (I) wherein A, R, W, Q, n and m have the meaning according to the claims can be employed, inter alia, for the treatment of tauopathies and Alzheimer's disease.

GLYCOSIDASE INHIBITORS

Compounds of formula (I) wherein A, R, W, Q, n and m have the meaning according to the claims can be employed, inter alia, for the treatment of tauopathies and Alzheimer's disease.

ACID ADDITION SALTS OF PIPERAZINE DERIVATIVES

The invention relates to acid addition salts of piperazine derivatives, as well as solid forms, such as polymorphic forms, thereof, which are useful as pharmaceutical ingredients and in particular as glycosidase inhibitors.

SUBSTITUTED PIPERAZINE COMPOUNDS AND METHODS OF USE AND USE THEREOF

The invention relates to substituted piperazine compounds and methods of use and uses thereof, and further to the pharmaceutical compositions comprising the compounds and uses thereof, wherein the compound has Formula (I) or a stereoisomer, a tautomer, an N-oxide, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof. The substituted piperazine compounds and pharmaceutical compositions comprising the compounds disclosed herein can be used for inhibiting 5-hydroxytryptamine reuptake and/or stimulating 5-HT1A receptors. The invention also relates to processes for preparing these compounds and pharmaceutical compositions, and their uses in the treatment of a central nervous system dysfunction.

NOVEL COMPOUNDS FOR USE IN COGNITION IMPROVEMENT

Novel compounds for use in cognition improvement It relates to certain compounds having a polycyclic structure and a -(C=O)NRaRb moiety, wherein the polycyclic structure comprises at least three ring systems, wherein one ring system is a polycyclic ring system comprising from 2 to 4 rings; at least one ring is an aromatic ring; and wherein the structure comprises at least 3 nitrogen atoms and 1 oxygen atom. It also relates to pharmaceutical compositions containing them, and to their use in medicine, in particular in the treatment and/or prevention of neurological disorders coursing with a cognition deficit or impairment, or neurodegenerative diseases.

Design, Synthesis, and Biological Evaluation of First-in-Class Dual Acting Histone Deacetylases (HDACs) and Phosphodiesterase 5 (PDE5) Inhibitors for the Treatment of Alzheimer's Disease

Simultaneous inhibition of phosphodiesterase 5 (PDE5) and histone deacetylases (HDAC) has recently been validated as a potentially novel therapeutic approach for Alzheimer's disease (AD). To further extend this concept, we designed and synthesized the first chemical series of dual acting PDE5 and HDAC inhibitors, and we validated this systems therapeutics approach. Following the implementation of structure- and knowledge-based approaches, initial hits were designed and were shown to validate our hypothesis of dual in vitro inhibition. Then, an optimization strategy was pursued to obtain a proper tool compound for in vivo testing in AD models. Initial hits were translated into molecules with adequate cellular functional responses (histone acetylation and cAMP/cGMP response element-binding (CREB) phosphorylation in the nanomolar range), an acceptable therapeutic window (>1 log unit), and the ability to cross the blood-brain barrier, leading to the identification of 7 as a candidate for in vivo proof-of-concept testing (Cuadrado-Tejedor, M.; Garcia-Barroso, C.; Sánchez-Arias, J. A.; Rabal, O.; Mederos, S.; Ugarte, A.; Franco, R.; Segura, V.; Perea, G.; Oyarzabal, J.; Garcia-Osta, A. Neuropsychopharmacology 2016, in press, doi: 10.1038/npp.2016.163).

GLYCOSIDASE INHIBITORS

Compounds of formula (I) wherein A, R, W, Q, n and m have the meaning according to the claims can be employed, inter alia, for the treatment of tauopathies and Alzheimer's disease.