158407-04-6

Basic information

• Product Name: 4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• Synonyms: 4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;1-N-BOC-4-BROMOMETHYLPIPERIDINE;1-BOC-4-BROMOMETHYLPIPERIDINE;4-Bromomethyl-piperidine-1-carboxylic acid tert-butyk ester;N-BOC-4-BROMOMETHYL-PIPERIDINE;tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate;4-Bromomethyl-1-(tert-butoxycarbonyl)piperidine;1-Piperidinecarboxylic acid, 4-(bromomethyl)-, 1,1-dimethylethyl ester
• CAS NO: 158407-04-6
• Molecular Formula: C₁₁H₂₀BrNO₂
• Molecular Weight: 278.19
• Product Categories: pharmacetical
• Mol File: 158407-04-6.mol

Chemical Properties

• Boiling Point: 318.337 °C at 760 mmHg
• Flash Point: 146.325 °C
• Appearance: /
• Density: 1.271 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.495
• Storage Temp.: Room temperature.
• PKA: -1.91±0.40(Predicted)
• CAS DataBase Reference: 4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(158407-04-6)
• EPA Substance Registry System: 4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(158407-04-6)

Safety Data

• Statements: 36/37/38-36
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 158407-04-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is used as an organic synthesis intermediate for the creation of various chemical compounds. Its unique structure allows for further functionalization and modification, enabling the development of new molecules with specific properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is used as a pharmaceutical intermediate. It plays a vital role in the development of new drugs, particularly those targeting the central nervous system, as it can be incorporated into the molecular structure of potential therapeutic agents. Its presence in the final drug molecule can contribute to the drug's efficacy, safety, and pharmacokinetic properties.
Used in Laboratory Research and Development:
4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is also utilized in laboratory research and development processes. Researchers use this compound to explore its potential applications in various fields, such as medicinal chemistry, drug design, and chemical biology. Through these studies, scientists can gain a deeper understanding of the compound's properties and how it can be harnessed for the development of new drugs and chemicals.
Used in Chemical Production Process:
In the chemical production process, 4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is employed as a key component in the synthesis of various chemicals. Its versatility and reactivity make it an essential building block for the production of a wide range of chemical products, including specialty chemicals, agrochemicals, and materials for various industrial applications.

Synthesis

4-Bromomethypiperidine-1-carboxylic acid tert-butyl ester. 4-N-Boc-piperidine-methanol (200 mg, 0.93 mmol) was dissolved in diethyl ether (9 mL) and carbon tetrabromide (370 mg, 1.1 mmol) and PPh3 (292 mg, 1.1 mmol) were added at rt. The reaction was allowed to stir for 18 h at rt and filtered over a pad of celite. The filtrate was concentrated and purified by flash chromatography (hexane/EtOAc, 1:0 → 4:1) to give the title compound. Yield 55 mg. 1 (400 MHz, DMSO-d6) δ ppm 4.02-3.98 (m, 2 H), 3.47 (d, 2 H), 2.78-2.65 (m, 2 H), 1.89-1.74 (m, 3 H), 1.45 (s, 9 H), 1.12-0.98 (m, 2 H).

InChI:InChI=1/C11H20BrNO2/c1-11(2,3)15-10(14)13-6-4-9(8-12)5-7-13/h9H,4-8H2,1-3H3

Upstream product

• 123855-51-6 tert-butyl 4-(hydroxymethyl)piperidin-1-carboxylate 
• 498-94-2 isonipecotic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 
• 161975-39-9 tert-butyl 4-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate 
• 6457-49-4 4-piperidinemethanol 
• 69719-84-2 4-(bromomethyl)piperidine 

Downstream Products

• 701299-13-0 tert-butyl 4-((2-methyl-1H-imidazol-1-yl)methyl)piperidine-1-carboxylate 
• 1067230-50-5 C₃₇H₅₈N₄O₆ 
• 176967-61-6 1-(tert-butoxycarbonyl)-4-(4-cyanophenoxymethyl)piperidine 
• 1076188-32-3 tert-butyl 4-((4-acetyl-3-methylphenoxy)methyl)piperidine-1-carboxylate 
• 1052100-52-3 3-[(N-tert-butoxycarbonylpiperidin-4-ylmethyl)(1-methyl-1H-imidazole-4-sulfonyl)amino]-N-(4-cyanophenyl)-N-(3-methyl-3H-imidazol-4-ylmethyl)propanamide 
• 145508-94-7 tert-butyl 4-(iodomethyl)piperidine-1-carboxylate 
• 1186615-60-0 N-(N-tert-butoxycarbonylpiperidin-4-ylmethyl), N-({2-[(4-cyanophenyl)-(3-methyl-3H-imidazol-4-ylmethyl)-amino]-ethyl})2-methylbenzenesulfonamide 
• 1239957-22-2 tert-butyl 4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)piperidine-1-carboxylate 
• 1174718-08-1 2-(4-chlorophenyl)-4-(N-Boc-4-piperidinemethyl)-thieno[2,3-d]pyridazinyl-7-ethyl formate 
• 1264296-64-1 tert-butyl 4-(2-(3-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-7-yl)-3-ethoxy-2-methyl-3-oxopropyl)piperidine-1-carboxylate 
• 1610417-13-4 tert-butyl 4-(((5-amino-4-methyl-1-phenyl-1H-pyrazol-3-yl)oxy)methyl)piperidine-1-carboxylate 

Relevant articles and documents

Structural requirements for TLR7-selective signaling by 9-(4-piperidinylalkyl)-8-oxoadenine derivatives

We report the synthesis and biological evaluation of a new series of 8-oxoadenines substituted at the 9-position with a 4-piperidinylalkyl moiety. In vitro evaluation of the piperidinyl-substituted oxoadenines 3a-g in human TLR7- or TLR8-transfected HEK293 cells and in human PBMCs indicated that TLR7/8 selectivity/potency and cytokine induction can be modulated by varying the length of the alkyl linker. Oxoadenine 3f containing a 5-carbon linker was found to be the most potent TLR7 agonist and IFNα inducer in the series whereas 3b possessing a 1-carbon linker was the most potent TLR8 agonist.

BROAD SPECTRUM ANTI-CANCER COMPOUNDS

Described herein, inter alia, are compounds for treating cancer and methods of use. This disclosure features chemical entities (e.g., small hairpin RNAs (shRNAs), micro RNA (miRNAs), small interfering RNA (siRNAs), small molecule inhibitors, antisense nucleic acids, peptides, viruses, CRISPR-sgRNAs, or combinations thereof) that inhibit one or more of m6A writers (e.g., methyltransferase like 3 (Mettl3 or MT-A70) or methyltransferase like-14 (Mettl14)), m6Am writers (e.g., phosphorylated CTD interacting factor I (PCIF 1), or Mettl3/14), m6A erasers (e.g., fat-mass and obesity-associated protein (FTO) or ALKB homolog 5 (ALKBH5)), m6Am erasers (e.g., FTO), m6A readers (e.g., YTH domain-containing family proteins (YTHs)), YTF domain family member 1 (YTHDF 1), YTF domain family member 2 (YTHDF 2), YTF domain family member 3 (YTHDF 3), or tyrosine-protein phosphatase non-receptor type 2 (PTPN2).

Identification of 2,4-Disubstituted Imidazopyridines as Hemozoin Formation Inhibitors with Fast-Killing Kinetics and in Vivo Efficacy in the Plasmodium falciparum NSG Mouse Model

A series of 2,4-disubstituted imidazopyridines, originating from a SoftFocus Kinase library, was identified from a high throughput phenotypic screen against the human malaria parasite Plasmodium falciparum. Hit compounds showed moderate asexual blood stage activity. During lead optimization, several issues were flagged such as cross-resistance against the multidrug-resistant K1 strain, in vitro cytotoxicity, and cardiotoxicity and were addressed through structure-Activity and structure-property relationship studies. Pharmacokinetic properties were assessed in mice for compounds showing desirable in vitro activity, a selectivity window over cytotoxicity, and microsomal metabolic stability. Frontrunner compound 37 showed good exposure in mice combined with good in vitro activity against the malaria parasite, which translated into in vivo efficacy in the P. falciparum NOD-scid IL-2Rnull (NSG) mouse model. Preliminary mechanistic studies suggest inhibition of hemozoin formation as a contributing mode of action.

Anodic oxidation of dithiane carboxylic acids: A rapid and mild way to access functionalized orthoesters

A new electrochemical methodology has been developed for the preparation of a wide variety of functionalized orthoesters under mild and green conditions from easily accessible dithiane derivatives. The new methodology also offers an unprecedented way to access tri(fluorinated) orthoesters, a class of compound that has never been studied before. This provides the community with a rapid and general method to prepare libraries of functionalized orthoesters from simple and readily available starting materials.

Compound with dual inhibitory activity TDO, IDOO1 and application of compound for treating neurodegenerative disease (by machine translation)

The present invention provides a compound of formula I, or a pharmaceutically acceptable salt thereof, or a solvate thereof, which can selectively inhibit TDO, IDOO1, which has a significant inhibitory effect on TDO and/or IDOO1. In addition, the prepared compound has a remarkable anti-tumor effect, has a certain treatment effect on's disease and's disease, and has a good application prospect in the field of medicine preparation. (by machine translation)

4 - Amino - pyrimidine and nitrogen heterocyclic derivatives and its preparation and use (by machine translation)

The invention belongs to the field of biological chemistry, and in particular relates to 4 - amino - pyrimidine and nitrogen heterocyclic derivatives and its preparation and use. The present invention provides a 4 - amino - pyrimidine and nitrogen heteroc

Design, synthesis and biological evaluation of 7H-pyrrolo[2,3-d]pyrimidin-4-amine derivatives as selective Btk inhibitors with improved pharmacokinetic properties for the treatment of rheumatoid arthritis

Bruton's tyrosine kinase (Btk) is a Tec family kinase with a well-defined role in the B cell receptor (BCR) and Fcγ receptor (FcR) signaling pathways, which makes it a uniquely attractive target for the treatment of autoimmune diseases, such as rheumatoid arthritis (RA). We reported a series of compounds bearing 7H-pyrrolo [2,3-d]pyrimidin-4-amine scaffold that potently inhibited Btk in vitro. Analysis of the structure-activity relationships (SAR) and drug-like profiles led to the discovery of the optimal compound B16. B16 preferentially inhibited Btk (IC50 = 21.70 ± 0.82 nM) over closely related kinases with moderate selectivity. Cell-based tests also confirmed that B16 significantly inhibited Btk Y223 auto-phosphorylation and PLCγ2 Y1217 phosphorylation. MTT revealed that B16 displayed weak suppression against normal LO2, HEK293 and THP-1 cell lines with IC50 values over 30 μM. Moreover, B16 showed very weak potential to block the hERG channel (IC50 = 11.10 μM) in comparison to ibrutinib (IC50 = 0.97 μM). Owing to its favorable physicochemical properties (ClogP = 2.53, aqueous solubility ≈ 0.1 mg/mL), pharmacokinetic profiles (F = 49.15%, t1/2 = 7.02 h) and reasonable CYP450 profile, B16 exhibited potent anti-arthritis activity and similar efficacy to ibrutinib in reducing paw thickness in CIA mice. In conclusion, B16 is a potent, selective and durable inhibitor of Btk and has the potential to a safe and efficacious treatment for arthritis.

PROCESS FOR THE PREPARATION OF ORGANIC BROMIDES

The present invention provides a process for the preparation of organic bromides, by a radical bromodecarboxylation of carboxylic acids with a bromoisocyanurate.

FUMAGILLOL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME

Disclosed herein, in part, are fumagillol compounds and methods of use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making fumagillol compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.

ADENINE DERIVATIVES WHICH ARE USEFUL IN THE TREATMENT OF ALLERGIC DISEASES OR OTHER INFLAMMATORY CONDITIONS

Compounds of formula (I).