1196713-67-3

Usage

Uses

Used in Pharmaceutical Synthesis:
Methyl 2-4-[(3S)-1-(tert-butoxycarbonyl)piperidin-3-yl]-phenyl-2H-indazole-7-carboxylate is utilized as an intermediate in the synthesis of various pharmaceuticals due to its unique structural components that can be manipulated to create a range of bioactive molecules.
Used in Drug Development:
As a compound with potential pharmacological activities, it serves as a candidate in drug development for possible therapeutic applications, pending further research into its biological effects and safety profile.
Used in Organic Chemistry Research:
In the field of organic chemistry, methyl 2-{4-[(3S)-1-(tert-butoxycarbonyl)piperidin-3-yl]-phenyl}-2H-indazole-7-carboxylate is used as a subject of study for understanding reaction mechanisms, synthesis strategies, and the exploration of new chemical methodologies.
Used in Medicinal Chemistry:
Methyl 2-4-[(3S)-1-(tert-butoxycarbonyl)piperidin-3-yl]-phenyl-2H-indazole-7-carboxylate is employed in medicinal chemistry for the design and optimization of new drugs, capitalizing on its structural features to target specific biological pathways or receptors.

Upstream product

• 1038916-05-0 tert-butyl (3S)-3-[4-({(1E)-[3-(methoxycarbonyl)-2-nitrophenyl]methylene}amino)phenyl]piperidine-1-carboxylate 
• 6340-79-0 4-oxo-4-(4-bromophenyl)butanoic acid 
• 1284448-67-4 isopropyl 4-(4-bromophenyl)-4-oxobutanoate 
• 1476776-39-2 isopropyl 3-(2-(4-bromophenyl)oxiran-2-yl)-propanoate 
• 1476776-40-5 isopropyl 4-(4-bromophenyl)-5-oxopentanoate 
• 1476776-44-9 (S)-5-(4-bromophenyl)piperidin-2-one 
• 1476776-53-0 (S)-3-(4-bromophenyl)piperidin-1-ium 4-methylbenzenesulfonate 
• 1335523-82-4 4-(3S-piperidine-3-yl)bromobenzene 
• 1476776-62-1 C₁₁H₁₆BrNO 
• 1476776-64-3 (S)-tert-butyl (2-(4-bromophenyl)-5-hydroxypentyl)carbamate 
• 1476776-66-5 (S)-4-(4-bromophenyl)-5-((tert-butoxycarbonyl)amino)pentyl methanesulfonate 
• 108-86-1 bromobenzene 
• 1476776-61-0 C₁₁H₁₃BrO₂ 
• 171364-83-3 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene 

Downstream Products

• 1038916-11-8 tert-butyl (3S)-3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}piperidine-1-carboxylate 
• 1038915-64-8 (3S)-3-[4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl]piperidinium chloride 
• 1038916-08-3 2-{4-[(3S)-1-(tert-butoxycarbonyl)piperidin-3-yl]phenyl}-2H-indazole-7-carboxylic acid 
• 1038915-60-4 (3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine 

Relevant academic research and scientific papers

Derivative based on PARP inhibitor Niraparib and a preparation method and use thereof

The invention discloses a derivative based on a PARP inhibitor Niraparib. The derivative has a structure shown in a formula I as shown in the description, wherein R1 is selected from alkyl, alkoxy, cycloalkyl, aryl alkyl, cycloalkyl alkyl, heterocyclyl, a

Method for preparing Niraparib of PARP (poly-ADP-ribose polymerase) inhibitor

The invention discloses a method for preparing 2-(4-((3S)-3-piperidyl) phenyl)-2H-indazole-7-formamide of a compound. Benzyl protected-piperidone is generated into piperidone of 3-triflic anhydride under the action of triflic anhydride, the piperidone and nitrobenzoic acid are subjected to Suzuki reaction to obtain a coupled product, 3-(4-aminophenyl) piperidine is obtained under the action of a palladium reagent, (S)-3-(4-halogenated phenyl) piperidine is prepared with a chirality resolution reagent, the (S)-3-(4-halogenated phenyl) piperidine is condensed with 3-formyl-2-methyl nitrobenzoate to form pyrazolone ring under the action of sodium azide, and the Niraparid (with the molecular entity of 2-(4-((3S)-3-piperidyl) phenyl)-2H-indazole-7-formamide) is prepared via aminolysis.

Preparation method of niraparib tosilate monohydrate

The invention discloses a preparation method of a compound 2-[4-((3S)-3-piperidyl)phenyl]-2H-indazole-7-formamide tosilate monohydrate. The method includes: carrying out Ulman reaction on 1H-indazole-7-methyl formate and (S)-3-(4-halogenophenyl)piperidine-1-tert-butyl formate to prepare 2-[4-((3S)-3-piperidyl)phenyl]-2H-indazole-7-methyl formate, then under the conditions of ammonia gas and p-toluenesulfonic acid, preparing 2-[4-((3S)-3-piperidyl)phenyl]-2H-indazole-7-formamide tosilate monohydrate. The invention aims to avoid the disadvantages of existing methods, shortens the preparation route, and provides the preparation method of the 2-[4-((3S)-3-piperidyl)phenyl]-2H-indazole-7-formamide tosilate monohydrate with high chiral purity, and the method has the characteristics of mild reaction and easy operation.

A prepares Nepal to pull handkerchief Nepal method (by machine translation)

The invention discloses a compound 2 - [4 - ((3S) - 3 - piperidinyl) phenyl] - 2H - indazole - 7 - carboxamide preparation method, through the 4 - nitro phenylpyridyl with reaction produced animal pen halogenphenmethyl season ammonium salt, by sodium borohydride reduction of the pyridine quaternary ammonium salt, in the palladium reagent obtained under the action of the 3 - (4 - aminophenyl) piperidine, in the chiral reagent obtained under the action of the (S)- 3 - (4 - halophenyl) piperidine, with 3 - formyl - 2 - nitro-benzoic acid methyl ester condensation and in sodium azide formed under the action of powder medicine, after preparing the amine Niraparib (molecular entity is: 2 - [4 - ((3S) - 3 - piperidinyl) phenyl] - 2H - indazole - 7 - carboxamide). (by machine translation)

Process development of C-N cross-coupling and enantioselective biocatalytic reactions for the asymmetric synthesis of niraparib

Process development of the synthesis of the orally active poly(ADP-ribose)polymerase inhibitor niraparib is described. Two new asymmetric routes are reported, which converge on a high-yielding, regioselective, copper-catalyzed Narylation of an indazole derivative as the late-stage fragment coupling step. Novel transaminase-mediated dynamic kinetic resolutions of racemic aldehyde surrogates provided enantioselective syntheses of the 3-aryl-piperidine coupling partner. Conversion of the C-N cross-coupling product to the final API was achieved by deprotection and salt metathesis to isolate the desired crystalline salt form.

Development of a fit-for-purpose large-scale synthesis of an oral PARP inhibitor

Compound (1) a poly(ADP-ribose)polymerase (PARP) inhibitor has been made by a fit-for-purpose large-scale synthesis using either a classical resolution or chiral chromatographic separation. The development and relative merits of each route are discussed,

Discovery of 2-{4-[(3S)-piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide (MK-4827): A novel oral poly(ADP-ribose)polymerase (PARP) inhibitor efficacious in BRCA-1 and -2 mutant tumors

We disclose the development of a novel series of 2-phenyl-2H-indazole-7- carboxamides as poly(ADP-ribose) polymerase (PARP) 1 and 2 inhibitors. This series was optimized to improve enzyme and cellular activity, and the resulting PARP inhibitors display antiproliferation activities against BRCA-1 and BRCA-2 deficient cancer cells, with high selectivity over BRCA proficient cells. Extrahepatic oxidation by CYP450 1A1 and 1A2 was identified as a metabolic concern, and strategies to improve pharmacokinetic properties are reported. These efforts culminated in the identification of 2-{4-[(3S)-piperidin-3-yl] phenyl}-2H-indazole-7-carboxamide 56 (MK-4827), which displays good pharmacokinetic properties and is currently in phase I clinical trials. This compound displays excellent PARP 1 and 2 inhibition with IC50 = 3.8 and 2.1 nM, respectively, and in a whole cell assay, it inhibited PARP activity with EC50 = 4 nM and inhibited proliferation of cancer cells with mutant BRCA-1 and BRCA-2 with CC50 in the 10-100 nM range. Compound 56 was well tolerated in vivo and demonstrated efficacy as a single agent in a xenograft model of BRCA-1 deficient cancer.