939986-76-2

Basic information

• Product Name: 4-(6-Chloro-pyriMidin-4-ylaMino)-piperidine-1-carboxylic acid tert-butyl ester, 98+% C14H21ClN4O2, MW: 312.80
• Synonyms: 4-(6-Chloro-pyriMidin-4-ylaMino)-piperidine-1-carboxylic acid tert-butyl ester, 98+% C14H21ClN4O2, MW: 312.80;4-[(6-Chloro-4-pyrimidinyl)amino]-1-piperidinecarboxylic acid tert-butyl ester;tert-Butyl 4-[(6-chloropyrimidin-4-yl)amino]piperidine-1-carboxylate
• CAS NO: 939986-76-2
• Molecular Formula: C14H21ClN4O2
• Molecular Weight: 312.79514
• Mol File: 939986-76-2.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.261
• CAS DataBase Reference: 4-(6-Chloro-pyriMidin-4-ylaMino)-piperidine-1-carboxylic acid tert-butyl ester, 98+% C14H21ClN4O2, MW: 312.80(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(6-Chloro-pyriMidin-4-ylaMino)-piperidine-1-carboxylic acid tert-butyl ester, 98+% C14H21ClN4O2, MW: 312.80(939986-76-2)
• EPA Substance Registry System: 4-(6-Chloro-pyriMidin-4-ylaMino)-piperidine-1-carboxylic acid tert-butyl ester, 98+% C14H21ClN4O2, MW: 312.80(939986-76-2)

Safety Data

• Hazardous Substances Data: 939986-76-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(6-Chloro-pyriMidin-4-ylaMino)-piperidine-1-carboxylic acid tert-butyl ester, 98+% C14H21ClN4O2, MW: 312.80 is used as an intermediate in drug development for the synthesis of potential therapeutic agents. Its unique structure, including the chloro-pyrimidine moiety and tert-butyl ester functional group, allows for further chemical modifications and the creation of new pharmaceutical compounds.
Used in Research Settings:
In research, 4-(6-Chloro-pyriMidin-4-ylaMino)-piperidine-1-carboxylic acid tert-butyl ester, 98+% C14H21ClN4O2, MW: 312.80 serves as a valuable compound for organic synthesis and biochemical studies. Its structural features make it a useful building block for the development of new organic compounds and for investigating various biochemical processes and interactions.

Upstream product

• 1193-21-1 4,6-dichloropyrimidine 
• 87120-72-7 1-(tert-butoxycarbonyl)-4-aminopiperidine 

Relevant articles and documents

Discovery of a novel series of GPR119 agonists: Design, synthesis, and biological evaluation of N-(Piperidin-4-yl)-N-(trifluoromethyl)pyrimidin-4-amine derivatives

We undertook an optimization effort involving propan-2-yl 4-({6-[5-(methanesulfonyl)-2,3-dihydro-1H-indol-1-yl]pyrimidin-4-yl}oxy)piperidine-1-carboxylate 1, which we had previously discovered as a novel G protein-coupled receptor 119 (GPR119) agonist. To occupy a presumed hydrophobic space between the pyrimidine and piperidine rings in interaction with GPR119, we replaced the linker oxygen with nitrogen. Subsequently, the introduction of a substituent at the bridging nitrogen atom was explored. We found that the installation of N-trifluoromethyl group 10 not only enhanced GPR119 agonist activity but also considerably improved the human ether-à-go-go-related gene (hERG) inhibition profile. These improvements were not observed for non-fluorinated substituents, such as ethyl analog 8b. The next optimization effort focused on the exploration of a new surrogate structure for the indoline ring and the isosteric replacements of the piperidine N-Boc group to improve solubility, metabolic stability, and oral bioavailability. As a result, N-{1-[3-(2-fluoropropan-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-4-yl}-6-{[1-(methanesulfonyl)piperidin-4-yl]oxy}-N-(trifluoromethyl)pyrimidin-4-amine (27) was identified as a potent and orally bioavailable GPR119 agonist. This compound augmented insulin secretion and effectively lowered plasma glucose excursion in a diabetic animal model after oral administration. In this study, we discuss the designs, syntheses, and biological activities of a novel series of N-(piperidin-4-yl)-N-(trifluoromethyl)pyrimidin-4-amine derivatives as GPR119 agonists, and to determine the distinctive effect of the N-trifluoromethyl group on hERG inhibition, we also discuss the conformational preference of representative compounds.