Schering Corporation

Schering-plough Corporation

Ramani R Raghavan

Jeonghan Park

Weidong Tong

George S K Wong

Anantha R Sudhakar

Minzhang Chen

Xiaojing Yang

Eugene John Vater

Ingyu Jeon

Juergen Weber

Maria M Tamarez

Daw-long Albert Kwok

George G Wu

Frank Xing Chen

Shen-Chun Kuo

Kartik M Keertikar

George S Wong

Hong-Chang Lee

Ji Xie

Daw-Jong Kwok

Disclosed is a process for the synthesis of compounds of Formula I by sequentially aminating, first with a primary amine and then with a secondary amine, an intermediate compound of the structure of Formula E1, wherein Ris a linear, branched, or cyclic alkyloxy functional group of the structure (&#x2014;R&#x2014;OH), Ris a linear, branched or cyclic alkyl group, Ris a linear, branched or cyclic alkyl group, and Ris an alkylene-heterocycle, said process comprising forming intermediate compound of Formula E1 by reacting, in a refluxing reaction solvent selected from alcohols having 5 or less carbon atoms and mixtures of two or more thereof, a methanol solution of a salt of a 4-alkyl-3-amino-pyrazole compound of Formula C1, with a diamidization reagent selected from dimethylmalonate, monomethylmalonyl-chloride, and malonyl dichloride in the presence of a Lewis base having sufficient proton affinity to abstract a proton from the 1-position nitrogen on the pyrazole ring.

Process and intermediates for the synthesis of (3-alkyl-5-piperidin-1-yl-3,3a-dihydro-pyrazolo[1,5-a]pyrimidin-7-yl)-amino derivatives and intermediates

In one embodiment, the present application relates to a process of making a compound of formula I. and to certain intermediate compounds that are made within the process of making the compound of formula I.

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Process and intermediates for the preparation of (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylates for salts thereof

In one embodiment, the present invention describes the synthesis of (4-bromophenyl) (4-piperidyl)methanone-(Z)-O-ethyloxime and its acid salts, and similar compounds, in high stereochemical purity.

Synthesis of (4-bromophenyl)(4-piperidyl)methanone-(Z)-O-ethyloxime and salts

Process and intermediates for the preparation of (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylates or salts thereof

In one embodiment, the present invention describes the synthesis of (4-bromophenyl) (4-piperidyl)methanone-(Z)&#x2014;O-ethyloxime and its acid salts, and similar compounds, in high stereochemical purity.

Synthesis of (4-bromopnenyl)(4-piperidyl)methanone-(Z)-O-ethyloxime and salts

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Hillside, NJ, United States of America

Ramani R Raghavan