50606-32-1

Basic information

• Product Name: N-(n-butoxycarbonyl)piperazine
• Synonyms: N-(n-butoxycarbonyl)piperazine;Butyl piperazine-1-carboxylate
• CAS NO: 50606-32-1
• Molecular Formula: C₉H₁₈N₂O₂
• Molecular Weight: 186.25142
• Mol File: 50606-32-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 141-143 °C(Press: 10 Torr)
• Appearance: /
• Density: 1.030±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 8.45±0.10(Predicted)
• CAS DataBase Reference: N-(n-butoxycarbonyl)piperazine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(n-butoxycarbonyl)piperazine(50606-32-1)
• EPA Substance Registry System: N-(n-butoxycarbonyl)piperazine(50606-32-1)

Safety Data

• Hazardous Substances Data: 50606-32-1(Hazardous Substances Data)

Usage

General Description

N-(n-butoxycarbonyl)piperazine, also known as Boc-piperazine, is a chemical compound used in the pharmaceutical industry as a building block for the synthesis of various compounds, including pharmaceuticals and agrochemicals. It is a derivative of piperazine, a heterocyclic organic compound, with a butoxycarbonyl (Boc) protecting group attached to the nitrogen atom. The Boc group serves as a protecting agent, allowing for specific reactions to occur at the unprotected sites of the piperazine molecule. Boc-piperazine is commonly used in the preparation of peptide and organic compounds, as well as in the development of novel drug candidates. It is also used as a reagent in organic synthesis and as a precursor in the manufacturing of pharmaceutical products. Overall, N-(n-butoxycarbonyl)piperazine is a versatile and important chemical that plays a crucial role in the synthesis of various pharmaceutical and agrochemical compounds.

Upstream product

• 1019928-96-1 4-benzylpiperazine-1-carboxylic acid butyl ester 
• 592-34-7 carbonochloridic acid, butyl ester 
• 1073554-07-0 piperazine-1,4-dicarboxylic acid tert-butyl ester butyl ester 
• 110-85-0 piperazine 

Downstream Products

• 1159502-62-1 4-[2-benzyloxycarbonylamino-2-(dimethoxy-phosphoryl)-acetyl]-piperazine-1-carboxylic acid butyl ester 
• 1021703-38-7 4-{(S)-4-tert-butoxycarbonyl-2-[(6-chloro-2-phenyl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid butyl ester 
• 1190713-25-7 3.3. 4-((S)-4-tert-butoxycarbonyl-2-{[6-((1S,2S)-2-methoxymethyl-cyclopropyl)-2-phenyl-pyrimidine-4-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid butyl ester 
• 1190713-15-5 4-((S)-4-carboxy-2-{[6-((1S,2S)-2-methoxymethylcyclopropyl)-2-phenylpyrimidine-4-carbonyl]amino}butyryl)piperazine-1-carboxylic acid butyl ester 
• 1019929-05-5 butyl (S)-4-(2-benzyloxycarbonylamino-4-tert-butoxycarbonylbutyryl)piperazine-1-carboxylate 

Relevant articles and documents

4-((R)-2-{[6-((S)-3-Methoxypyrrolidin-1-yl)-2-phenylpyrimidine-4-carbonyl]amino}-3-phosphonopropionyl)piperazine-1-carboxylic Acid Butyl Ester (ACT-246475) and Its Prodrug (ACT-281959), a Novel P2Y12 Receptor Antagonist with a Wider Therapeutic Window in the Rat Than Clopidogrel

Recent post hoc analyses of several clinical trials with P2Y12 antagonists showed the need for new molecules being fully efficacious as antiplatelet agents and having a reduced propensity to cause major bleeding. We have previously reported the discovery of the 2-phenylpyrimidine-4-carboxamide analogs as P2Y12 antagonists with nanomolar potency in the disease-relevant platelet aggregation assay in human plasma. Herein we present the optimization steps that led to the discovery of clinical candidate ACT-246475 (30d). The key step was the replacement of the carboxylic acid functionality by a phosphonic acid group which delivered the most potent molecules of the program. In addition, low in vivo clearance in rat and dog was achieved for the first time. Since the bioavailability of 30d was low in rat and dog, we developed the bis((isopropoxycarbonyl)oxy)methyl ester prodrug (ACT-281959, 45). Compound 30d showed efficacy in the rat ferric chloride thrombosis model when administered intravenously as parent or orally as its prodrug 45. Moreover, 30d displays a wider therapeutic window as compared to clopidogrel in the rat surgical blood loss model.

2-PHENYL-6-AMINOCARBONYL-PYRIMIDINE DERIVATIVES AND THEIR USE AS P2Y12 RECEPTOR ANTAGONISTS

The invention relates to 2-phenyl-6-aminocarbonyl-pyrimidine derivatives and their use as P2Y12 receptor antagonists in the treatment and/or prevention and/or treatment of peripheral vascular, of visceral-, hepatic- and renal-vascular, of cardiovascular and of cerebrovascular diseases or conditions associated with platelet aggregation, including thrombosis in humans and other mammals. Formula (I).

Piperazinyl glutamate pyridines as potent orally bioavailable P2Y 12 antagonists for inhibition of platelet aggregation

Polymer-assisted solution-phase (PASP) parallel library synthesis was used to discover a piperazinyl glutamate pyridine as a P2Y12 antagonist. Exploitation of this lead provided compounds with excellent inhibition of platelet aggregation as measured in a human platelet rich plasma (PRP) assay. Pharmacokinetic and physiochemical properties were optimized through modifications at the 4-position of the pyridine ring and the terminal nitrogen of the piperazine ring, leading to compound (4S)-4-[({4-[4-(methoxymethyl) piperidin-1-yl]-6-phenylpyridin-2-yl}carbonyl)amino]-5-oxo-5-{4-[(pentyloxy) carbonyl]piperazin-1-yl}pentanoic acid 47s with good human PRP potency, selectivity, in vivo efficacy, and oral bioavailability. Compound 47s was selected for further preclinical evaluations.