1146629-75-5

Usage

Uses

Used in Pharmaceutical Synthesis:
(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate is used as a heterocyclic derivative for pharmaceutical synthesis. Its unique chemical structure makes it a valuable building block for the development of new drugs, particularly those targeting specific biological pathways or receptors. The presence of the chlorine atom and the pivalate group allows for further functionalization and modification, enabling the creation of a diverse range of pharmaceutically relevant compounds.
In the pharmaceutical industry, (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate is used as a key intermediate in the synthesis of various therapeutic agents. Its incorporation into drug molecules can potentially enhance their pharmacological properties, such as potency, selectivity, and bioavailability. Additionally, (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate may be utilized in the development of novel drugs for the treatment of various diseases, including cancer, neurological disorders, and infectious diseases, among others.
Furthermore, (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate can also be employed in the design of prodrugs, which are biologically inactive compounds that are converted into active drugs within the body. This approach can improve the pharmacokinetic properties of the final drug, such as its solubility, stability, and absorption, ultimately leading to better therapeutic outcomes for patients.

Upstream product

• 18997-19-8 Chloromethyl pivalate 
• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 55052-28-3 4-chloro-7-azaindole 

Downstream Products

• 1146629-77-7 [4-(1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]methyl 2,2-dimethylpropanoate 
• 1187594-09-7 Baricitinib 
• 1187595-90-9 (4-{1-[3-(cyanomethyl)-1-(ethylsulphonyl)azetidin-3-yl]-1H-pyrazol-4-yl}-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl 2,2-dimethylpropanoate 
• 1298084-48-6 (4-(6-(3-nitrophenyl)-1H-indole-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-7-yl)methyl pivalate 
• 1298084-30-6 N-(3-(1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-indol-6-yl)phenyl)-4-chloro-3-(trifluoromethyl)benzamide 
• 1298084-29-3 1-(3-(1-(7H-pyrrolo[2,3-d]pyrimidine-4-yl)-1H-indole-6-yl)phenyl)-3-(2-methoxyphenyl)urea 
• 1298084-47-5 (4-(6-(3-aminophenyl)-1H-indole-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-7-yl)methyl pivalate 

Relevant academic research and scientific papers

Synthesis and Characterization of Compounds Potentially Related to the Janus Kinase Inhibitor Baricitinib

Nine compounds potentially related to the Janus kinase inhibitor Baricitinib have been identified, synthesized by conventional methods, and characterized by IR, 1H and 13C NMR, and mass spectral data.

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.

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.

BARICITINIB INTERMEDIATE, METHOD FOR FORMING BARICITINIB INTERMEDIATE, AND METHOD FOR PREPARING BARICITINIB OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF

The present disclosure provides a Baricitinib intermediate, a method for preparing the Baricitinib intermediate, and a method for preparing Baricitinib or a pharmaceutically acceptable salt thereof using the Baricitinib intermediate. The method for preparing the Baricitinib intermediate involves the use of a divalent palladium catalyst or a nickel catalyst and provides the Baricitinib intermediate in high yield.

JAK KINASE INHIBITOR AND PREPARATION METHOD AND USE THEREOF

Provided in the present invention are a new type JAK kinase selective inhibitor and a preparation method and the use thereof. In particular, disclosed are a compound having the structure as shown in chemical formula (I) as a JAK kinase inhibitor or a stereoisomer or a tautomer thereof, or a pharmaceutically acceptable salt, a hydrate or a solvate thereof.

CML THERAPEUTIC AGENTS WITH REDUCED DRUG-RESISTANCE AND SIDE-EFFECT COMPRISING 1,6-DISUBSTITUTED INDOLE COMPOUNDS

The present invention relates to a therapeutic agent for chronic myelogenous leukemia with reduced drug-resistance and side-effects containing a 1,6-disubstituted indole compound.

Preparation method for intermediate of Baricitinib

The invention discloses a preparation method for an intermediate of Baricitinib. The intermediate of Baricitinib has a chemical structural formula represented by a formula (I) shown in the description, wherein X is a toluenesulfonate group, a trifluoromethanesulfonate group, chloro-, iodo- or bromo-, and R1 is a group resistant to room-temperature acidic conditions. The preparation method for the intermediate of Baricitinib is characterized by comprising the steps: mixing a compound represented by a formula (II) shown in the description, alkali and a solvent, and carrying out a hydrogen extracting reaction so as to obtain a reaction solution, wherein the alkali is sodium tert-butoxide, potassium tert-butoxide, lithium tert-butoxide, sodium amide or lithium amide; dropwise adding R1Cl into the reaction solution; and carrying out stirring, carrying out a quenching reaction, and carrying out aftertreatment. According to the preparation method, the reaction conditions are mild, the operation is simple, potential risks existing during reactions are greatly reduced, and the disadvantage that mineral oil in sodium hydrogen is not easily detected and the like is overcome. The preparation method is applicable to industrial production and has a very great popularization value.

PROCESS FOR THE PREPARATION OF BARICITINIB AND AN INTERMEDIATE THEREOF

The present invention provides a process for the preparation of baricitinib and an intermediate thereof. The present invention provides a convenient, economical, and industrially advantageous two-step process for the preparation of [4-(IH-pyrazol-4-yl)-7Hpyrrolo[2,3-d] pyrimidin-7-yl]methyl pivalate of Formula (II). The process of the present invention involves the use of an alkali or alkaline earth metal hydroxide, carbonate, or bicarbonate as a base for reacting 4-chloro-7H-pyrrolo[2,3-d]pyrimidine of Formula (III) with chloromethyl pivalate of Formula (IV), and the use of an unprotected pyrazole borolane of Formula (VIII) for the conversion of (4-chloro-7H-pyrrolo[2,3-d] pynmidin-7- yl)methyl 2,2-dimethylpropanoate of Formula V into [4-(1 H-pyrazol-4-yl)-7Hpyrrolo[2,3-d]pyrimidin-7-yl]methyl pivalate of Formula (II). The process of the present invention provides [4-(1 H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]methyl pivalate of Formula (I) in high yield.

NOVEL 1,6-DISUBSTITUTED INDOLE COMPOUNDS AS PROTEIN KINASE INHIBITORS

Disclosed are a 1,6-substituted indole compound having a protein kinase inhibition activity, a pharmaceutically acceptable salt, and a pharmaceutical composition for prevention and treatment of cancers caused by abnormal cell growth comprising the compoun

NOVEL 1,6-DISUBSTITUTED INDOLE COMPOUNDS AS PROTEIN KINASE INHIBITORS

Disclosed are a 1,6-substituted indole compound having a protein kinase inhibition activity, a pharmaceutically acceptable salt, and a pharmaceutical composition for prevention and treatment of cancers caused by abnormal cell growth comprising the compoun