923565-98-4

Basic information

• Product Name: (S)-1-N-CBZ-2-METHYL-PIPERAZINE
• Synonyms: REF DUPL: (S)-1-N-Cbz-2-methyl-piperazine;1-Piperazinecarboxylic acid, 2-Methyl-, phenylMethyl ester, (2S)-;(S)-2-Methyl-1-piperazinecarboxylic acid benzyl ester;Benzyl (2S)-2-methyl-1-piperazinecarboxylate;(S)-1-Cbz-2-Methyl-piperazine HCl
• CAS NO: 923565-98-4
• Molecular Formula: C13H18N2O2
• Molecular Weight: 234.297
• Mol File: 923565-98-4.mol

Chemical Properties

• Boiling Point: 358°C at 760 mmHg
• Flash Point: 170.3°C
• Appearance: /
• Density: 1.105
• Vapor Pressure: 2.62E-05mmHg at 25°C
• Refractive Index: 1.53
• PKA: 8.48±0.40(Predicted)
• CAS DataBase Reference: (S)-1-N-CBZ-2-METHYL-PIPERAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-N-CBZ-2-METHYL-PIPERAZINE(923565-98-4)
• EPA Substance Registry System: (S)-1-N-CBZ-2-METHYL-PIPERAZINE(923565-98-4)

Safety Data

• Hazardous Substances Data: 923565-98-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry Research:
(S)-1-N-CBZ-2-METHYL-PIPERAZINE is used as a research compound for studying its chemical properties and potential applications in organic chemistry. Its unique structure and protected nitrogen atom make it an interesting subject for investigation.
Used in Pharmaceutical Industries:
(S)-1-N-CBZ-2-METHYL-PIPERAZINE is used as a key intermediate in the synthesis of various pharmaceutical drugs. Its protected nitrogen atom and chiral configuration allow for the development of enantiomerically pure compounds, which are often required for drug efficacy and safety.
Used in Drug Synthesis:
(S)-1-N-CBZ-2-METHYL-PIPERAZINE is used as a building block in the synthesis of new drug candidates. Its protected nitrogen atom and methyl substitution on the piperazine ring provide a versatile platform for further chemical modifications, potentially leading to the discovery of novel therapeutic agents.

InChI:InChI=1/C13H18N2O2/c1-11-9-14-7-8-15(11)13(16)17-10-12-5-3-2-4-6-12/h2-6,11,14H,7-10H2,1H3/t11-/m0/s1

Upstream product

• 109-07-9 (RS)-2-methylpiperazine 
• 501-53-1 benzyl chloroformate 
• 1163793-31-4 1-benzyl 4-(tert-butyl) (S)-2-methylpiperazine-1,4-dicarboxylate 
• 1163793-25-6 1-benzyl 4-(tert-butyl) (R)-2-methylpiperazine-1,4-dicarboxylate 
• 243982-41-4 (R)-3-methyl-1-((2-nitrophenyl)sulfonyl)piperazine 
• 75336-86-6 (2R)-methylpiperazine 
• 1025927-13-2 (R)-2-Methyl-4-(2-nitro-benzenesulfonyl)-piperazine-1-carboxylic acid benzyl ester 

Relevant articles and documents

Design, synthesis and SAR of antitubercular benzylpiperazine ureas

Abstract: N-furfuryl piperazine ureas disclosed by scientists at GSK Tres Cantos were chosen as antimycobacterial hits from a phenotypic whole-cell screen. Bioisosteric replacement of the furan ring in the GSK Tres Cantos molecules with a phenyl ring led to molecule (I) with an MIC of 1?μM against Mtb H37Rv, low cellular toxicity (HepG2 IC50 ~ 80?μM), good DMPK properties and specificity for Mtb. With the aim of delineating the SAR associated with (I), fifty-five analogs were synthesized and screened against Mtb. The SAR suggests that the piperazine ring, benzyl urea and piperonyl moieties are essential signatures of this series. Active compounds in this series are metabolically stable, have low cellular toxicity and are valuable leads for optimization. Molecular docking suggests these molecules occupy the Q0 site of QcrB like Q203. Graphic Abstract: Bioisosteric replacement of N-furfuryl piperazine-1-carboxamides yielded molecule (I) a novel lead with satisfactory PD, metabolism, and toxicity profiles.[Figure not available: see fulltext.]

SUBSTITUTED BENZAMIDES AND METHODS OF USE THEREOF

The invention provides compounds having the general formula I, and pharmaceutically acceptable salts thereof, wherein the variables RA, RAA, subscript n, ring A, X2, L, subscript m, X1, R1, R2, R3, R4, R5, and RN have the meaning as described herein, and compositions containing such compounds and methods for using such compounds and compositions.

CERTAIN CHEMICAL ENTITIES, COMPOSITIONS AND METHODS

Certain substituted urea derivatives selectively modulate the cardiac sarcomere, for example by potentiating cardiac myosin, and are useful in the treatment of systolic heart failure including congestive heart failure.

PROCESS FOR PRODUCING OXYCARBONYL-SUBSTITUTED PIPERAZINE DERIVATIVE

If an organic solvent with a water content of 15% or less is used when an oxycarbonyl-substituted piperazine derivative is produced from a piperazine derivative, the piperazine derivative can be oxycarbonylated.

Secondary amides of (R)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid as inhibitors of pyruvate dehydrogenase kinase

N'-Methyl-N-(4-tert-butyl-1,2,5,6-tetrahydropyridine)thiourea, SDZ048- 619 (1), is a modest inhibitor (IC50 = 180 μM) of pyruvate dehydrogenase kinase (PDHK). In an optimization of the N-methylcarbothioamide moiety of 1, it was discovered that amides with a small acyl group, in particular appropriately substituted amides of (R)-3,3,3-trifluoro-2-hydroxy-2- methylpropionic acid, are inhibitors of PDHK. Utilizing this acyl moiety, herein is reported the rationale leading to the optimization of a series of acylated piperazine derivatives. Methyl substitution of the piperazine at the 2- and 5-positions (with S and R absolute stereochemistry) markedly increased the potency of the lead compound (> 1000-fold). Oral bioavailability of the compounds in this series is good and is optimal (as measured by AUC) when the 4-position of the piperazine is substituted with an electron-poor benzoyl moiety. (+)-1-N-[2,5-(S,R)-Dimethyl-4-N-(4-cyanobenzoyl)piperazine]-(R)- 3,3,3-trifluoro-2-hydroxy-2-methylpropanamide (14e) inhibits PDHK in the primary enzymatic assay with an IC50 of 16 ± 2 nM, enhances the oxidation of [14C]lactate into 14CO2 in human fibroblasts with an EC50 of 57 ± 13 nM, diminishes lactate significantly 2.5 h post-oral-dose at doses as low as 1 μmol/kg, and increases the ex vivo activity of PDH in muscle, liver, and fat tissues in normal Sprague-Dawley rats. These PDHK inhibitors, however, do not lower glucose in diabetic animal models.