54527-65-0

Usage

Uses

Used in Pharmaceutical Industry:
2-(Benzylmethylamino)ethyl acetoacetate is used as an intermediate in the synthesis of Nicardipine O-Desmethyl-O-methyl(phenylmethyl)aminoethyl Ester Hydrochloride (N394510), which is a Nicardipine (N394500) impurity. Nicardipine is a dihydropyridine calcium channel blocker with applications as an antianginal and antihypertensive agent.
Used in Chemical Industry:
2-(Benzylmethylamino)ethyl acetoacetate is used as an intermediate for the syntheses of different organic chemicals, contributing to the development of a wide range of products in the chemical industry. Its unique chemical properties make it a versatile building block for creating various compounds with specific applications.
For more information on the specific uses and attributes of 2-(benzylmethylamino)ethyl acetoacetate, it is recommended to contact the relevant experts or suppliers in the field.

InChI:InChI=1/C14H19NO3/c1-12(16)11-14(17)18-10-9-15-8-7-13-5-3-2-4-6-13/h2-6,15H,7-11H2,1H3

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 101-98-4 2-(N-benzyl-N-methyl)amino-1-ethanol 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 103-67-3 benzyl-methyl-amine 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 101041-83-2 2-Methyl-5-oxo-4-thiazol-2-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid 2-(benzyl-methyl-amino)-ethyl ester 
• 106720-63-2 2-[[2-(trifluoromethyl)phenyl]methylene]-3-oxobutanoic acid, 2-[methyl(phenylmethyl)amino]ethyl ester 
• 54527-73-0 2-(N-benzyl-N-methylamino)-ethyl 3-aminocrotonate 
• 54527-98-9 2-[(3-nitrophenyl)methylene]-3-oxobutanoic acid, 2-[methyl(phenylmethyl)amino]ethyl ester 
• 96995-99-2 5-(2,3-Dichloro-phenyl)-1,3,7-trimethyl-4-oxo-2-thioxo-1,2,3,4,5,8-hexahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid 2-(benzyl-methyl-amino)-ethyl ester 
• 145695-46-1 2,6-Dimethyl-4-(9-oxo-9H-fluoren-4-yl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-[2-(benzyl-methyl-amino)-ethyl] ester 5-ethyl ester 
• 142731-05-3 2,6-Dimethyl-4-(9-oxo-9H-xanthen-4-yl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-[2-(benzyl-methyl-amino)-ethyl] ester 5-ethyl ester 
• 54527-84-3 nicardipine hydrochloride 
• 1442442-66-1 C₂₂H₂₅N₃O₃ 
• 54527-99-0 1,2,6-trimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-β-(N-benzyl-N-methylamino)ethyl ester 5-methyl ester hydrochloride 
• 54527-77-4 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-isopropylester-5-β-(N-benzyl-N-methylamino)-ethyl ester hydrochloride 
• 54527-95-6 2,6-dimethyl-4-(o-trifluoromethyl-phenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-β-(N-benzyl-N-methylamino)ethyl ester 5-methyl ester hydrochloride 
• 54585-91-0 5-acetyl-2,6-dimethyl-4-(3'-trifluoromethylphenyl)-1,4-dihydropyridine-3-carboxylic acid β-(N-benzyl-N-methylamino)ethyl ester hydrochloride 
• 109232-80-6 3-cyclopropylmethyl 5-[2-(N-benzyl-N-methylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate 

Relevant academic research and scientific papers

Synthesis and Evaluation of 3,4-Dihydropyrimidin-2(1H)-ones as Sodium Iodide Symporter Inhibitors

The sodium iodide symporter (NIS) is responsible for the accumulation of iodide in the thyroid gland. This transport process is involved in numerous thyroid dysfunctions and is the basis for human contamination in the case of exposure to radioactive iodine species. 4-Aryl-3,4-dihydropyrimidin-2(1H)-ones were recently discovered by high-throughput screening as the first NIS inhibitors. Described herein are the synthesis and evaluation of 115 derivatives with structural modifications at five key positions on the pyrimidone core. This study provides extensive structure-activity relationships for this new class of inhibitors that will serve as a basis for further development of compounds with invivo efficacy and adequate pharmacokinetic properties. In addition, the SAR investigation provided a more potent compound, which exhibits an IC50 value of 3.2nM in a rat thyroid cell line (FRTL5).

Photocyclization of 2-(dialkylamino)ethyl acetoacetates: Remote proton transfer and stern-volmer quenching kinetics in the system involving two reactive excited states

Upon irradiation, 2-(dibenzylamino)ethyl and 2-(N-benzyl-N-methylamino)ethyl acetoacetate (1a and 1b) undergo photocyclization via remote proton transfer from the benzyl group to the acetyl carbonyl oxygen to give eight-membered azalactones. Irradiation of the corresponding (diisopropylamino)- and (dimethylamino)ethyl esters gave no azalactones. Introduction of the methyl group on C-2 of 1a brought about a complicated photoreaction, probably due to competition of α-cleavage. The Stern-Volmer plots for the photoreaction of 1a did not show the linear relationship indicating that the photoreaction proceeds from two reactive excited states. The Stern-Volmer quenching equation for the system was obtained by applying the steady-state approximation and was used for the analysis of the photoreaction of 1a. The triplet lifetime was determined to be 1.6 × 10-8 s.

Novel 2-amino-1,4-dihydropyridine calcium antagonists. II. Synthesis and antihypertensive effects of 2-amino-1,4-dihydropyridine derivatives having N,N-dialkylaminoalkoxycarbonyl groups at 3- and/or 5-positions

Novel 2-amino-1,4-dihydropyridine derivatives I, which contain N,N-dialkylaminoalkoxycarbonyl groups at the 3- and/or 5-position, were synthesized and their antihypertensive effects were evaluated in spontaneously hypertensive rats. Remarkably prolonged duration of antihypertensive action was observed when a tertiary amino group was introduced into either the 3- or 5-ester side-chain of the 1,4-dihydropyridine ring. In particular, the compounds containing cyclic amino moieties at the 3-position showed greater potency than those with acyclic amino moieties. Chemical modification studies indicated that the two ester side-chains of 1,4-dihydropyridine at the 3- and 5-position might function in a different manner in relation to the antihypertensive activities. 3-(1-Benzhydrylazetidin-3-yl) 5-isopropyl 2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxyl ate, I-43 (CS-905), exhibited potent and long-lasting antihypertensive effects with gradual onset of action, and is a promising candidate as an antihypertensive drug.

Novel halogenated 1,4-dihydropyridines: synthesis, bioassay, microsomal oxidation and structure-activity relationships

Nine new 1,4-dihydropyridines (DHPs) were synthesized and evaluated for their relaxant ability (rat aorta) and their antihypertensive activity in spontaneously hypertensive rats; their microsomal oxidation rate (MOR) was determined.In terms of relaxant activity, the 4-(3,5-difluorophenyl) analogues were more potent than those with 4-(4-fluorophenyl) but weaker than those with 4-(3-nitrophenyl) substituents, while in terms of antihypertensive activity the 4-(3,5-difluorophenyl) derivatives were more potent than their 4-(3-nitrophenyl) analogues.Their MOR could beexplained the basis of the electron-withdrawing effect of the substituents, and in some cases they permitted a rationalization of discrepancies noted between DHP antihypertensive and relaxant activities.A parabolic relationship was found between the size of the carboxylic ester substituents and their contributions calculated from a Free-Wilson/Fujita-Ban analysis of relaxant activity data. 1,4-dihydropyridine / aorta relaxant activity / antihypertensive activity / microsomal oxidation rate / structure-activity relationship.

Applications of Stevens [1,2]-shifts of cyclic ammonium ylides. A route to morpholin-2-ones

2-(N,N-Dialkylamino)ethyl diazoacetoacetates 2 were prepared in two steps from readily available ethanolamines 1 . When heated in the presence of catalytic Cu, the substrates cleanly formed morpholinones 3, presumably via the intermediacy of copper cathenoids and cyclic ammonium ylides. In most cases involving benzylic or allylic migrating groups, ylide [1,2]-shift occurred in good yield (55-80%). In the case of benzhydryl containing substrate 2g, only dimer 4 was isolated. Simple alkyl groups failed to undergo the rearrangement, with the exception of tert-butyl case 2i, which furnished morpholinone 3i in low yield. Substituted allylic case 21 gave only [1,2]-shift product 3l, with no evidence for competing [2,3]-shift to give 3l'. Diazoacetates 2n-p also underwent conversion to morpholinones 3n-p in 19-64% yield with Cu(acac)2 catalysis.