519028-33-2

Usage

Uses

Used in Pharmaceutical Development:
Benzyl (2-(4-((4-fluorobenzyl)carbamoyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-yl)carbamate is used as a chemical intermediate for the synthesis of pharmaceutical drugs. Its unique structure, including the carbamoyl and 4-fluorobenzyl groups, may contribute to the development of new therapeutic agents with specific biological activities.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, Benzyl (2-(4-((4-fluorobenzyl)carbamoyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-yl)carbamate serves as a valuable compound for studying the structure-activity relationships of potential drug candidates. Its synthesis and modification can provide insights into the design of novel pharmaceuticals with improved efficacy and safety profiles.
Used in Drug Discovery:
Benzyl (2-(4-((4-fluorobenzyl)carbamoyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-yl)carbamate is utilized in drug discovery processes to identify new lead compounds with potential therapeutic applications. Its unique chemical features may offer novel mechanisms of action or target specific biological pathways, leading to the development of innovative treatments for various diseases.
Used in Chemical Synthesis:
In the chemical synthesis industry, Benzyl (2-(4-((4-fluorobenzyl)carbamoyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-yl)carbamate can be employed as a building block or reactant in the preparation of more complex organic molecules. Its versatile structure allows for further functionalization and modification, enabling the synthesis of a wide range of chemical products with diverse applications.

Upstream product

• 519032-08-7 methyl 2-(1-{[(benzyloxy) carbonyl] amino}-1-methylethyl)-5,6-dihydroxypyrimidine-4-carboxylate 
• 140-75-0 para-fluorobenzylamine 
• 1064707-10-3 C₁₈H₂₃N₃O₇ 
• 1028026-73-4 C₁₈H₂₃N₃O₇ 
• 518047-98-8 [1-(N'-hydroxycarbamimidoyl)-1-methyl-ethyl]carbamic acid benzyl ester 
• 501-53-1 benzyl chloroformate 
• 100134-82-5 (cyano-dimethyl-methyl)carbamic acid benzyl ester 
• 1064707-10-3 2-[(2-benzyloxycarbonylamino-2-methyl-propionimidoyl)-aminooxy]-but-2-enedioic acid dimethyl ester 
• 518047-98-8 benzyl [2-amino-2-(hydroxyimino)-1,1-dimethylethyl]carbamate 

Downstream Products

• 519028-28-5 5,6-dihydroxy-2-(1-methyl-1-methylamino-ethyl)-pyrimidine-4-carboxylic acid 4-fluoro-benzylamide 
• 519032-35-0 2-(1-benzylamino-1-methyl-ethyl)-5,6-dihydroxy-pyrimidine-4-carboxylic acid 4-fluoro-benzylamide 
• 519032-37-2 2-{1-[benzyl(methyl)amino]-1-methylethyl}-N-(4-fluorobenzyl)-5,6-dihydroxypyrimidine-4-carboxamide 
• 518048-02-7 {1-[4-(4-fluoro-benzylcarbamoyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidin-2-yl]-1-methyl-ethyl}carbamic acid benzyl ester 
• 518048-05-0 raltegravir 
• 1328839-28-6 C₂₄H₂₃FN₈O₇ 
• 1172131-65-5 C₂₉H₃₃FN₄O₆ 
• 1172131-64-4 2,2-dimethyl-propionic acid 2-(1-amino-1-methyl-ethyl)-4-(4-fluorobenzylcarbamoyl)-1-methyl-6-oxo-1,6-dihydropyrimidin-5-yl ester 
• 1172131-66-6 C₂₅H₂₉FN₆O₆ 
• 519028-40-1 C₂₄H₂₅FN₄O₅ 
• 518048-03-8 2-(1-amino-1-methyl-ethyl)-N-[(4-fluorophenyl)methyl]-1,6-dihydro-5-hydroxy-1-methyl-6-oxo-4-pyrimidinecarboxamide 
• 519028-41-2 2-(1-amino-1-methylethyl)-N-(4-fluorobenzyl)-5,6-dihydroxypyrimidine-4-carboxamide 

Relevant academic research and scientific papers

Development of a second-generation, highly efficient manufacturing route for the HIV integrase inhibitor raltegravir potassium

A manufacturing route for the synthesis of raltegravir potassium 1 was developed via a thermal rearrangement of amidoxime DMAD adducts 6 to construct the key, highly functionalized hydroxypyrimidinone core 7. Utilizing this route 1 was prepared in nine linear chemical steps with 22% overall yield. A second-generation synthesis was subsequently developed that solved the key chemical, productivity, and environmental impact issues of the initial synthesis. Highlights of the new synthesis include a highly selective methylation, 3-4-fold higher productivity, and a 65% reduction of combined organic and aqueous waste produced. The efficient second-generation manufacturing route provides raltegravir potassium 1 in 35% overall yield.

PROCESS FOR PREPARING N-SUBSTITUTED HYDROXYPYRIMIDINONE CARBOXAMIDES

Processes for preparing certain N-arylalkyl-1-(alkyl or aralkyl)-2-acylaminoalkyl- 5-hydroxy -6-oxo-1,6-dihydropyrimidine-4-carboxamides are disclosed. In one embodiment, the process comprises acylating the free amine in the corresponding N-arylalkyl-1-(alkyl or aralkyl)- 2-aminoalkyl-5-ester protected hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxamide and then deprotecting the 5-hydroxy by base hydrolysis. The hydroxypyrimidinone carboxamide products of the process are HTV integrase inhibitors which are useful for treating HTV infection, treating AIDS, or delaying the onset or progression of AIDS. Certain esterified N-arylalkyl hydroxypyrimidinone carboxamides that can be employed as process intermediates are also disclosed.

Dihydroxypyrimidine-4-carboxamides as novel potent and selective HIV integrase inhibitors

Human immunodeficiency virus type-1 (HIV-1) integrase, one of the three constitutive viral enzymes required for replication, is a rational target for chemotherapeutic intervention in the treatment of AIDS that has also recently been confirmed in the clinical setting. We report here on the design and synthesis of N-benzyl-5,6-dihydroxypyrimidine-4-carboxamides as a class of agents which exhibits potent inhibition of the HIV-integrase-catalyzed strand transfer process. In the current study, structural modifications on these molecules were made in order to examine effects on HIV-integrase inhibitory potencies. One of the most interesting compounds for this series is 2-[1-(dimethylamino)-1-methylethyl]-N-(4-fluorobenzyl)-5,6-dihydroxypyrimidine- 4-carboxamide 38, with a CIC95 of 78 nM in the cell-based assay in the presence of serum proteins. The compound has favorable pharmacokinetic properties in preclinical species (rats, dogs, and monkeys) and shows no liabilities in several counterscreening assays, highlighting its potential as a clinically useful antiviral agent.

4,5-Dihydroxypyrimidine carboxamides and N-alkyl-5-hydroxypyrimidinone carboxamides are potent, selective HIV integrase inhibitors with good pharmacokinetic profiles in preclinical species

The dihydroxypyrimidine carboxamide 4a was discovered as a potent and selective HIV integrase strand transfer inhibitor. The optimization of physicochemical properties, pharmacokinetic profiles, and potency led to the identification of 13 in the dihydroxypyrimidine series and 18 in the N-methylpyrimidinone series having low nanomolar activity in the cellular HIV spread assay in the presence of 50% normal human serum and very good pharmacokinetics in preclinical species.