181955-79-3

Basic information

• Product Name: 1,4-BIS(N-BOC)PIPERAZINE-2-CARBOXYLIC ACID
• Synonyms: 1,4-DI-BOC-PIPERAZINE-2-(+/-)-CARBOXYLIC ACID;1,4-BIS(N-BOC)PIPERAZINE-2-CARBOXYLIC ACID;1,4-bis-Boc-piperazine-2-carboxylic acid;1-N-Boc-4-N-Boc-piperazine-2-carboxylic acid;Piperazine-1,2,4-tricarboxylic acid 1,4-di-tert-butyl ester;1,2,4-Piperazinetricarboxylic acid, 1,4-bis(1,1-dimethylethyl) ester;1,2,4-Piperazinetricarboxylic acid 1,4-bis(tert-butyl) ester;1,4-Di-Boc-piperazine-2-carboxylic acid, 97.5%
• CAS NO: 181955-79-3
• Molecular Formula: C₁₅H₂₆N₂O₆
• Molecular Weight: 330.38
• Mol File: 181955-79-3.mol

Chemical Properties

• Melting Point: 142-148°C
• Boiling Point: 443.888 °C at 760 mmHg
• Flash Point: 222.256 °C
• Appearance: /
• Density: 1.201 g/cm³
• Vapor Pressure: 4.05E-09mmHg at 25°C
• Refractive Index: 1.502
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,4-BIS(N-BOC)PIPERAZINE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-BIS(N-BOC)PIPERAZINE-2-CARBOXYLIC ACID(181955-79-3)
• EPA Substance Registry System: 1,4-BIS(N-BOC)PIPERAZINE-2-CARBOXYLIC ACID(181955-79-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 181955-79-3(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C15H26N2O6/c1-14(2,3)22-12(20)16-7-8-17(10(9-16)11(18)19)13(21)23-15(4,5)6/h10H,7-9H2,1-6H3,(H,18,19)

Upstream product

• 2762-32-5 piperazine-2-carboxylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 3022-15-9 piperazine-2-carboxylic acid dihydrochloride 
• 497-19-8 sodium carbonate 
• 73371-96-7 2-<<(tert-butoxycarbonyl)oxy>imino>-2-phenylacetonitrile 
• 171504-98-6 O₁,O₄-di-tert-butyl O₂-methyl piperazine-1,2,4-tricarboxylate 

Downstream Products

• 143540-05-0 2-hydroxymethylpiperazine-1,4-dicarboxylic acid di-tert-butyl ester 
• 935544-54-0 1-phenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one 
• 935544-47-1 tert-butyl 3-oxotetrahydro-1H-oxazolo[3,4-a]pyrazine-7(3H)-carboxylate 
• 847554-73-8 tert-butyl 3-oxo-1-phenyltetrahydro-1H-oxazolo[3,4-a]pyrazine-7(3H)-carboxylate 
• 927883-45-2 2-carbamoylpiperazine-1,4-dicarboxylic acid di-tert-butyl ester 
• 1093345-77-7 di-tert-butyl 2-{[(2,6-dimethylphenyl)amino]carbonyl}piperazine-1,4-dicarboxylate 
• 171504-98-6 O₁,O₄-di-tert-butyl O₂-methyl piperazine-1,2,4-tricarboxylate 
• 1092478-40-4 (+/-)-bis(1,1-dimethylethyl) 2-[3-(ethyloxy)-3-oxopropyl]-2-methyl-1,4-piperazinedicarboxylate 
• 1609464-37-0 C₂₂H₂₆ClN₃O₅ 
• 1609464-36-9 C₂₂H₂₇ClN₄O₄ 

Relevant articles and documents

Method for synthesizing monoamine-protected piperazine-(R/S)2-formate

The invention discloses a method for synthesizing monoamine-protected piperazine-(R/S)2-formate, wherein the method comprises the steps: by using 2-piperazinecarboxylate as a raw material, protecting1,4-site amines by using different protective groups, and salifying by using different chiral amines, resolving to obtain a single chiral compound; and finally, using pyridine or DMAP and other pyridine analogues as an alkali, reacting oxalyl chloride, triphosgene, phosgene, thionyl chloride and other similar acyl chlorides in anhydrous tetrahydrofuran, 2-methyl tetrahydrofuran or toluene and other solvents, and finally adding methanol, ethanol, isopropanol, benzyl alcohol and other alcohol reagents to generate the target product capable of removing carboxylic acid ortho-amino protecting groups in a positioned manner and esterifying carboxylic acid. Amino groups on piperazine are separately protected through simple three-step reaction, chiral resolution is performed by utilizing the characteristics of acid, finally, protonated intermediates are formed through organic alkali and carboxylic acid, anhydride is formed by the protonated intermediates and ortho-amino groups, formic acid esterification is performed by utilizing alcohol to replace ring opening, and a final product is obtained.

Bis(vinylsulfonyl)piperazines as efficient linkers for highly homogeneous antibody-drug conjugates

Disulfide re-bridging strategy has demonstrated significant advantages in the construction of homogeneous antibody drug conjugates (ADCs). However, a major issue that disulfide scrambling at the hinge region of antibody leads to the formation of “half-antibody” has appeared for many re-bridging linkers. We present bis(vinylsulfonyl)piperazines (BVP) as efficient linkers to selectively re-bridge disulfides at the antigen-binding fragment (Fab) regions and produce highly homogeneous conjugates with a loading of two drugs without disulfide scrambling. We also found that optically active (S)-configuration linkers led to more sufficient conjugation compared with (R)-configuration. The BVP-linked ADCs demonstrated superior efficacy and antigen-selectivity in vitro cytotoxicity.

Piperazine compound and application thereof in preparation of chemokine receptor CCR2 antagonist

The invention relates to a piperazine compound as shown in a formula (I) and an application of the piperazine compound in preparation of a chemokine receptor CCR2 antagonist or a medicine for treatingCCR2-mediated diseases.

Hitting a Moving Target: Simulation and Crystallography Study of ATAD2 Bromodomain Blockers

Small molecule ligand binding to the ATAD2 bromodomain is investigated here through the synergistic combination of molecular dynamics and protein crystallography. A previously unexplored conformation of the binding pocket upon rearrangement of the gatekeeper residue Ile1074 has been found. Further, our investigations reveal how minor structural differences in the ligands result in binding with different plasticity of the ZA loop for this difficult-to-drug bromodomain.

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having potency in the modulation of NMDA receptor activity. Such compounds can be used in the treatment of conditions such as depression and related disorders. Orally delivered formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling

The direct union of primary, secondary, and tertiary carboxylic acids with a chiral glyoxylate-derived sulfinimine provides rapid access into a variety of enantiomerically pure α-amino acids (>85 examples). Characterized by operational simplicity, this radical-based reaction enables the modular assembly of exotic α-amino acids, including both unprecedented structures and those of established industrial value. The described method performs well in high-throughput library synthesis, and has already been implemented in three distinct medicinal chemistry campaigns.

Application of piperazine structure containing compound to preparation of LSD1 (Lysine Specific Demethylase 1) inhibitor

The invention discloses application of a piperazine structure containing compound to the preparation of a histone lysine specific demethylase (LSD1) inhibitor. The structural general formula of the compound is as shown in the following descriptions (wherein, A is hydrogen, carbonyl or thiocarbonyl) or a configurational isomer and a pharmaceutical salt thereof, or is as shown in the following descriptions or a pharmaceutical salt thereof. The compound has an obvious inhibition effect on the LSD1, can be prepared into the LSD1 inhibitor, and is used for preventing and treating a disease related to the activity of the histone LSD1.

Discovery of novel 2-((pyridin-3-yloxy)methyl)piperazines as α7 nicotinic acetylcholine receptor modulators for the treatment of inflammatory disorders

Herein we report the design, synthesis, and structure-activity relationships for a new class of α7 nicotinic acetylcholine receptor (nAChR) modulators based on the 2-((pyridin-3-yloxy)methyl)piperazine scaffold. The oxazolo[4,5-b]pyridine, (R)-18, and 4-methoxyphenylurea, (R)-47, were identified as potent and selective modulators of the α7 nAChR with favorable in vitro safety profiles and good oral bioavailability in mouse. Both compounds were shown to significantly inhibit cellular infiltration in a murine model of allergic lung inflammation. Despite the structural and in vivo functional similarities in the compounds, only (R)-18 was shown to be an agonist. Compound (R)-47 demonstrated silent agonist activity. These data support the hypothesis that the anti-inflammatory activity of the α7 nAChR is mediated by a signal transduction pathway that is independent of ion current.

COVALENT INHIBITORS OF KRAS G12C

Irreversible inhibitors of G12C mutant K-Ras protein are provided. Also disclosed are methods to modulate the activity of G12C mutant K-Ras protein and methods of treatment of disorders mediated by G12C mutant K-Ras protein.

PIPERAZINE DERIVATIVES AS CAV2.2 CALCIUM CHANNEL BLOCKERS

The invention relates to novel piperazine compounds; to processes for their preparation; to pharmaceutical compositions containing the compounds; and to the use of the compounds in therapy to treat diseases for which blocking the Cav2.2 calcium channels is beneficial, i.e. in particular to treat pain.