74053-94-4

Upstream product

• 2879-20-1 1,4-benzodioxan-6-yl methyl ketone 
• 105-58-8 Diethyl carbonate 
• 1197-09-7 1-(3,4-dihydroxyphenyl)ethan-1-one 
• 4442-54-0 2,3-dihydro-1,4-benzodioxin-6-carboxylic acid 
• 64-17-5 ethanol 
• 1404449-41-7 5-(2,3-dihydrobenzo[b][1,4]dioxine-6-carbonyl)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 6148-64-7 ethyl potassium malonate 
• 1282295-32-2 C₁₂H₁₀N₂O₃ 
• 6761-70-2 2,3-dihydro-1,4-benzodioxine-6-carbonyl chloride 

Downstream Products

• 491833-28-4 (1R,2R)-2-amino-1-(2,3-dihydrobenzo[β][1,4]dioxin-6-yl)-3-pyrrolidin-1-yl-propan-1-ol 
• 491833-29-5 (1R,2R)-octanoic acid [2-(2',3'-dihydro-benzo[1,4]dioxin-6'-yl)-2-hydroxy-1-pyrrolidin-1-ylmethyl-ethyl]-amide 
• 1607425-77-3 2-benzyl-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one 
• 1404447-17-1 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1404447-12-6 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1404447-07-9 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(4-fluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1404447-11-5 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1404447-29-5 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-hydroxy-3-phenylpyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1404447-43-3 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-phenyl-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1404447-30-8 3-(4-bromophenyl)-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1404446-58-7 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-phenylpyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1404446-60-1 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1404447-08-0 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1404447-18-2 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(3-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-7(4H)-one 

Relevant academic research and scientific papers

Eliglustat intermediate and preparation method thereof

The invention relates to an eliglustat intermediate and a preparation method thereof, and provides a series of intermediate compounds for preparing eliglustat, and a preparation method of the intermediates. With the method provided by the invention, raw materials and a transition metal catalyst are subjected to an asymmetric hydrogenation reaction on under certain conditions, and then a series ofreactions are performed to prepare eliglustat. The method provided by the invention is simple and controllable in reaction conditions and easy for industrial production.

Development of an Efficient and Scalable Asymmetric Synthesis of Eliglustat via Ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation

An efficient and scalable synthesis of eliglustat (1) is herein reported. This novel route features a three-step telescoped process to afford the α-dibenzylamino β-ketoester 6 in 85% overall yield from commercially available 1,4-benzodioxane-6-carboxylic acid 7. The key intermediate 5 was obtained via an efficient ruthenium-catalyzed DKR-ATH reaction, which afforded the desired product in 90% isolated yield with >99:1 dr and 99.7% ee on a 100 g scale. In addition, the amidation of sterically hindered carboxylic acid 14 was optimized and amenable to scale-up. This process not only gives a desirable total yield but also avoids hazardous conditions and chromatographic purification. The robustness of this synthesis was successfully performed on a multigram scale to afford 1 with >99.9% de and >99.9% ee in 56.8% overall yield in nine steps.

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

Unusual behaviour of 7-diethylamino-3-(3,4-ethylen-dioxybenzoyl)coumarin towards Group IIA cations: A potential photoactive probe for magnesium

The titled compound showed, upon spectrophotometric titrations with Group II cations, a spectacular bathochromic shift (c.a. 50 nm) with Mg2+ but not with the other cations. This result is - understood in terms of internal charge-transfer species expressly favored by Et2N and ArCO substituents and best matching of ionic diameter and charge density of Mg2+. This finding may lead to new simple photoactive probes.

Pyrrolidine-3-carboxylic acids as endothelin antagonists. 2. Sulfonamide-based ET(A)/ET(B) mixed antagonists

When the N,N-dialkylacetamide side chain of the highly ET(A)-selective endothelin antagonist ABT-627 (1; [2R,3R,4S]-2-(4-methoxyphenyl)-4-(1,3- benzodioxol-5-yl)-1-[[(N,N-dibutylamino)carbonyl]methyl]pyrrolidine-3- carboxylic acid; A-147627) is replaced by N,S-dialkylsulfonami-doethyl, the resultant analogs retain ET(A) affinity, but exhibit substantial ET(B) affinity as well. Structure-activity studies reveal that modifications in the length of the two alkyl groups, and in the substitution on the anisyl ring, are important in optimizing this 'balanced' antagonist profile. In particular the combination of an N-n-propyl group, an S-alkyl chain between four and six carbons in length, and a fluorine atom ortho to the aromatic OCH3 provides compounds with sub-nanomolar affinities for both receptor subtypes, and with ET(A)/ET(B) ratios close to 1. A number of these compounds also exhibit oral bioavailabilities (in rats) in the 30-50% range and have substantial plasma half-lives. The balanced receptor-binding profile of these potent and orally bioavailable compounds complements the ET(A) selectivity observed with 1.