94094-49-2

Usage

InChI:InChI=1/C9H11NO4S/c1-6(11)8-5-7(3-4-9(8)12)10-15(2,13)14/h3-5,10,12H,1-2H3

Upstream product

• 104-94-9 4-methoxy-aniline 
• 51-66-1 4-methoxyacetanilide 
• 7298-67-1 5-acetamido-2-hydroxyacetophenone 
• 57471-32-6 5-amino-2-hydroxyacetophenone hydrochloride 
• 124-63-0 methanesulfonyl chloride 
• 50-80-6 5-amino-2-hydroxyacetophenone 

Downstream Products

• 136079-88-4 (+) Methanesulfonamide, N-[1'-(6-cyano-1,2,3,4-tetrahydro-2-naphthalenyl)-3,4-dihydro-4-oxospiro[2H-1-benzopyran-2,4'-piperidin]-6-yl]- 
• 136080-55-2 1'-benzoyl-3,4-dihydro-6-methanesulfonamido-spiro[(2H)-1-benzopyran-2-4'-piperidine]-4-one 

Relevant academic research and scientific papers

Asymmetric Synthesis of MK-0499

Described herein is an efficient asymmetric synthesis of the potent antiarrhthymia agent MK-0499.The route is convergent and is highlighted by two stereoselective reactions.A ruthenium-catalyzed, enantioselective hydrogenation of an enamide was developed for the preparation of the key amine intermediate.Oxazaborolidine-mediated ketone reduction was utilized to establish the alcohol stereochemistry.Optimization of this chemistry led to an IPA modified reduction method which provides enhanced stereoselectivity.

Spirocycles

Spirocycles of the general structural formulae: STR1 wherein: X is O, CH2 or SOm ; R1 is AlkylSO2 NH--, AlkylO--, AlkylSO2 --, AlkylCONH--, or NO2 --; R2 is --H, --OAlkyl, or --Alkyl; R3 is --NHCOCH2 SOm Phenyl, --NHCOCH2 SOm Alkyl, --NHCOC(CH3)2 OH, or NHSO2 Alkyl; R4 and R5 are --H, or --Alkyl; R6 is STR2 R7 is --H, --CN, --NHSO2 Alkyl, --Br, --OAlkyl, --NH2, --NO2, --NHCOAlkyl, or NHCONHAlkyl; R8 is --H, --OH, --CN, --OAlkyl, --CONHAlkyl, --NHSO2 Alkyl, --NHCOAlkyl, --SOm Alkyl, or --CO2 Alkyl; and m is 0-2; or a pharmaceutically acceptable salt, hydrate or crystal form thereof; which are Class III antiarrhythmic agents.

NITROGEN-CONTAINING SPIROCYCLES

Spirocycles of general structural formula: STR1 are Class III antiarrhythmic agents.