877399-73-0

Basic information

• Product Name: 1-Piperidinecarboxylic acid, 4-(4-iodo-1H-pyrazol-1-yl)-, 1,1-dimethylethyl ester
• Synonyms: 1-Piperidinecarboxylic acid, 4-(4-iodo-1H-pyrazol-1-yl)-, 1,1-dimethylethyl ester;tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate;1-(4-BOC-piperazino)-4-iodopyrazole;1-(4-BOC-piperidyl)-4-iodopyrazole;1-Boc-4-(4-iodo-1H-pyrazol-1-yl)piperidine;4-(4-Iodo-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester;tert-Butyl 4-(4-iodopyrazolyl)piperidinecarboxylate;1-Piperidinecarboxylic acid, 4-(4-iodo-1H-pyrazol-1-yl)-
• CAS NO: 877399-73-0
• Molecular Formula: C₁₃H₂₀IN₃O₂
• Molecular Weight: 377.22
• Mol File: 877399-73-0.mol

Chemical Properties

• Melting Point: 97 °C
• Boiling Point: 430.596°C at 760 mmHg
• Flash Point: 214.217°C
• Appearance: /Solid
• Density: 1.603g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: 2-8°C(protect from light)
• PKA: 1.08±0.19(Predicted)
• Sensitive: Light Sensitive
• CAS DataBase Reference: 1-Piperidinecarboxylic acid, 4-(4-iodo-1H-pyrazol-1-yl)-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperidinecarboxylic acid, 4-(4-iodo-1H-pyrazol-1-yl)-, 1,1-dimethylethyl ester(877399-73-0)
• EPA Substance Registry System: 1-Piperidinecarboxylic acid, 4-(4-iodo-1H-pyrazol-1-yl)-, 1,1-dimethylethyl ester(877399-73-0)

Safety Data

• Hazardous Substances Data: 877399-73-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
1-Piperidinecarboxylic acid, 4-(4-iodo-1H-pyrazol-1-yl)-, 1,1-dimethylethyl ester is used as a building block for the development of new drugs and agrochemicals. Its unique chemical structure and properties make it a valuable component in the creation of pharmaceuticals and biologically active compounds.
Used in Organic Synthesis:
In the field of organic synthesis, 1-Piperidinecarboxylic acid, 4-(4-iodo-1H-pyrazol-1-yl)-, 1,1-dimethylethyl ester is used as a starting material for the production of various pharmaceuticals and biologically active compounds. Its potential therapeutic activities contribute to the advancement of drug discovery and development efforts.
Used in Drug Discovery:
1-Piperidinecarboxylic acid, 4-(4-iodo-1H-pyrazol-1-yl)-, 1,1-dimethylethyl ester is employed as a key component in drug discovery, where its unique properties and potential therapeutic activities are leveraged to create innovative and effective pharmaceuticals.
Used in Agrochemical Development:
In the agrochemical industry, 1-Piperidinecarboxylic acid, 4-(4-iodo-1H-pyrazol-1-yl)-, 1,1-dimethylethyl ester is used as a building block for the development of new agrochemicals, contributing to the creation of more effective and environmentally friendly products.

InChI:InChI=1/C13H20IN3O2/c1-13(2,3)19-12(18)16-6-4-11(5-7-16)17-9-10(14)8-15-17/h8-9,11H,4-7H2,1-3H3

Upstream product

• 3469-69-0 4-iodopyrazole 
• 141699-59-4 1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate 
• 189205-49-0 4-methanesulfonylpiperidine-1-carboxylic acid tert-butyl ester 
• 5382-16-1 4-HYDROXYPIPERIDINE 
• 24608-52-4 tert-butyl chloroformate 
• 109384-19-2 t-butyl 4-hydroxy piperidine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1229457-94-6 4-(4-iodo-1H-pyrazol-1-yl)piperidine 
• 118811-07-7 tert-butyl 4-(tosyloxy)piperidin-1-carboxylate 

Downstream Products

• 877399-74-1 tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate 
• 877399-52-5 crizotinib 
• 1428476-86-1 4-(4-{6-amino-5-[(R)-1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester 
• 1190875-39-8 (1-{1-[(tert-butoxy)carbonyl]piperidin-4-yl}-1H-pyrazol-4-yl)boronic acid 
• 1613332-92-5 3-((2,5-difluorophenyl)ethynyl)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine 
• 1613333-44-0 4-(4-(3-((2,5-difluorophenyl)ethynyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-1-yl)piperidine1-carboxylic acid tert-butyl ester 
• 1613332-90-3 3-((2,5-dichlorophenyl)ethynyl)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine 
• 1613333-43-9 4-(4-(3-((2,5-dichlorophenyl)ethynyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-1-yl)piperidine1-carboxylic acid tert-butyl ester 
• 1613333-41-7 4-(4-(1-(phenylsulfonyl)-3-((trimethylsilyl)ethynyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester 
• 1613333-40-6 4-(4-(3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-1-yl)piperidine1-carboxylic acid tert-butyl ester 
• 1613332-89-0 3-((2-chlorophenyl)ethynyl)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2.3-b]pyridine 
• 1613333-39-3 4-(4-(3-((2-chlorophenyl)ethynyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazole-1-yl)piperidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Preparation method of tert-butyl 4-(4-halo-1H-pyrazol-1-yl)piperidin-1-carboxylate

The invention discloses a preparation method of a crizotinib intermediate tert-butyl 4-(4-halo-1H-pyrazol-1-yl)piperidin-1-carboxylate, and belongs to the field of synthesis of medical intermediates.Tert-butyl 4-hydroxypiperidin-1-carboxylate is used as a raw material, the raw material and 4-halogenated pyrazole undergo a Mitsunobu reaction in the presence of triphenylphosphine and azodicarboxylic acid derivatives, an acid is added to adjust the pH, an intermediate 4-(4-halo-1H-pyrazol-1-yl)piperidine hydrochloride is obtained, alkaline dissociation is carried out, and meanwhile, Boc protection is carried out so that the tert-butyl 4-(4-halo-1H-pyrazol-1-yl)piperidin-1-carboxylate is obtained. The method has the advantages of simple process, cheap and easily available raw materials, highreaction selectivity, avoidance of elimination of byproducts, and simple post-treatment. The recrystallized tert-butyl 4-(4-halo-1H-pyrazol-1-yl)piperidin-1-carboxylate of a crude product has high purity and yield of 98.5% or above.

Hydrochloride of [1, 2, 4] triazine and [6,1-a] isoindole compound and application thereof

The invention belongs to the field of chemical medicines, and relates to a [1,2,4]triazine[6,1-a]isoindole compound with ALK/C-MET kinase duplex restraining activity, a pharmaceutical composition containing the compound and application of the compound or the composition in medicine preparation, in particular to hydrochloride and application of the [1,2,4]triazine[6,1-a]isoindole compound. The compound has good dissolubility and stability, and a better option is provided for dosage form research.

Pyrrolo[2, 3-d] pyrimidine derivatives containing piperidine as well as preparation and application thereof

The invention relates to a piperidine-containing pyrrolo[2, 3-d] pyrimidine derivative as shown in a general formula I or a general formula II as well as a use method and a preparation method thereof.The invention also relates to a strong JAK kinase inhibition effect of the compound shown in the general formula I or II, the invention also relates to an application of the compound in preparation of medicines for treating and/or preventing diseases caused by abnormal expression of JAK, and particularly relates to application of the compound in preparation of medicines for treating inflammatory/autoimmune diseases, fibrosis and cancers.

INDOLINONE COMPOUNDS FOR USE AS MAP4K1 INHIBITORS

The present disclosure is directed to compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein ring A, ring C, X1, X2, L1, R1, R2, R3, R4, R5, R6, R7, m and n are as defined herein, which are useful as MAP4K1 inhibitors, processes for their preparation, pharmaceutical compositions comprising the compounds, and the use of the compounds or the compositions in the treatment or prevention of various diseases, conditions and/or disorders mediated by MAP4K1.

PYRIMIDINE PYRAZOLYL DERIVATIVES AND THEIR USE AS IRAK INHIBITORS

The present invention provides compounds of Formula (II) for the treatment of cancer, rheumatoid arthritis and other diseases.

Design, synthesis and anti-inflammatory evaluation of novel pyrrolo[2,3-d]pyrimidin derivatives as potent JAK inhibitors

Aiming to develop potent JAK inhibitors, two series of 4-(1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidine derivatives (8a–8p and 11a–11i) were designed and synthesized by coalescing various N-acylpiperidine motifs with baricitinib. The pharmacological results based on enzymatic and cellular assays identified the optimized compound 11e, which exerted over 90% inhibition rates against JAK1 and JAK2, and displayed the most compelling anti-inflammatory efficacy superior to baricitinib by inhibiting NO generation from LPS-induced RAW264.7 macrophages. Importantly, low cytotoxity of 11e was revealed by the IC50 value of 88.2 μM against normal RAW264.7 cells. The binding mode of 11e with JAK1 and JAK2 identified the essential structural bases in accord with SARs analysis. Furthermore, cellular morphology observation and western blot analysis disclosed the ability of 11e to relieve cells inflammatory damage by significantly down-regulating LPS-induced high expression of JAK1, JAK2, as well as pro cytokine IL-1β. Together, 11e was verified as a promising lead for JAK inhibitors for the treatment of inflammatory diseases.

Alkenyl compound and its method and use thereof

The invention provides a new substituted alkenyl compound, pharmaceutically acceptable salts of the new substituted alkenyl compound, a medicinal preparation of the new substituted alkenyl compound, and application of the new substituted alkenyl compound, the pharmaceutically acceptable salts and the medicinal preparation of the new substituted alkenyl compound in aspects of regulating the activity of protein kinase and regulating the intercellular or intracellular signal response. The invention also relates to a medicament composition containing the compound at the same time, and relates to a method for treating high-proliferative diseases of mammals especially the human by using the medicament composition.

Alkynyl compound and its method and use thereof

The invention provides a novel substituted alkynyl compound and its pharmaceutically acceptable salt and medicinal preparation, and a use of the novel substituted alkynyl compound and its pharmaceutically acceptable salt and medicinal preparation in adjustment of protein kinase activity and intercellular or intracellular signal response. The invention also relates to a pharmaceutical composition containing the novel substituted alkynyl compound and a method for treating high-proliferative diseases of mammals especially such as human by the pharmaceutical composition.

Preparation method of crizotinib intermediate

The invention discloses a synthetic method of anti-tumor molecular targeted drug crizotinib, belongs to the field of pharmaceuticals, and relates to a synthetic method of a crizotinib intermediate. The method comprises two reduction processes: a bromination reaction process comprises the following reaction steps: a reduction process I: carrying out reduction reaction on a (R)-3-[1-(2,6-dichloro-3-fluorophenyl)ethoxyl]-2-nitropyridine compound and sodium dithionate under a mechanical chemical condition to generate (R)-3-[1-(2,6-dichloro-3-fluorophenyl)ethoxyl]-2-aminopyridine; a reduction process II: dissolving the (R)-3-[1-(2,6-dichloro-3-fluorophenyl)ethoxyl]-2-nitropyridine compound into an organic solvent, carrying out catalytic hydrogenation and reduction treatment to generate (R)-3-[1-(2,6-dichloro-3-fluorophenyl)ethoxyl]-2-aminopyridine; the bromination reaction process comprises a step of carrying out reaction between the compound and potassium hydrogen persulfate as well as bromate to obtain the crizotinib intermediate. The process is low in cost, the raw materials are easy to purchase, the operation is simple, convenient and safe, and the yield is high; moreover, the process is suitable for large-scale production.

Synthetic method of bis-4-(1H-pyrazol-1-yl) piperidine-1-tert-butyl formate and application thereof

The invention discloses a synthetic method of bis-4-(1H-pyrazol-1-yl) piperidine-1-tert-butyl formate and an application thereof. The bis-4-(1H-pyrazol-1-yl) piperidine-1-tert-butyl formate is prepared through a methyl sulfonylation reaction, a hydrocarbylation reaction, a Grignard reaction and a Suzuki coupling reaction by taking cheap and easily available N-Boc-4-hydroxyl piperidine as a raw material. The synthetic method is simple, the process is easy to control, and the yield of the prepared bis-4-(1H-pyrazol-1-yl) piperidine-1-tert-butyl formate is 86.7%; bis-4-(1H-pyrazol-1-yl) piperidine-1-tert-butyl formate can be used as a standard substance to detect and monitor synthesis of crizotinib. The synthetic method disclosed by the invention is suitable for synthesizing bis-4-(1H-pyrazol-1-yl) piperidine-1-tert-butyl formate and the synthesized substance is used for detecting and monitoring synthesis of crizotinib.