Syngenta Participations Ag

Miroslav Terinek

Helmars Smits

Tomas Smejkal

Christian Lothschuetz

Dominik Faber

Stefan Koenig

The present invention relates to processes for the preparation of substituted cycloserine compounds of formula (I) wherein Ris C-Calkyl, C-Chaloalkyl, C-Ccycloalkyl, aryl or aryl substituted by one to five R, or aryl-C-Calkylene or aryl-C-Calkylene substituted by one to five R; andeach Ris independently C-Calkyl, C-Chaloalkyl, C-Calkoxy, C-Chaloalkoxy, cyano or halogen; The invention also relates to intermediates produced by the processes. Compounds of formula (I) are useful intermediates for the production of compounds in the agricultural and pharmaceutical fields.

Process for the preparation of substituted cycloserines

The present invention relates to processes for the preparation of substituted cycloserine compounds of formula (I) wherein Ris C-Calkyl, C-Chaloalkyl, C-Ccycloalkyl, aryl or aryl substituted by one to five R, or aryl-C-Calkylene or aryl-C-Calkylene substituted by one to five R; and each Ris independently C-Calkyl, C-Chaloalkyl, C-Calkoxy, C-Chaloalkoxy, cyano or halogen; The invention also relates to intermediates produced by the processes. Compounds of formula (I) are useful intermediates for the production of compounds in the agricultural and pharmaceutical fields.

The invention relates to a process for the preparation of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide by acylating the oxime oxygen of the compound of formula (VIII), in the presence of a solvent and an acylating agent of formula (XI) RC(X)&#x2014;CI (XI); wherein X is oxygen or sulfur; Ris chloro if X is oxygen or sulfur; or R1 is C-Calkoxy, CH&#x2014;C(&#x2550;CH)&#x2014;O&#x2014;, phenoxy or trichloromethoxy if X is oxygen; and a) if Ris chloro and the compound of formula (XI) was added to the compound of formula (VIII); reacting the so obtained product of formula (XIIa) wherein X is oxygen or sulfur; with the compound of formula (IX) b) if Ris chloro and the compound of formula (VIII) was added to the compound of formula (XI); or Ris C-Calkoxy, CH&#x2014;C(&#x2550;CH)&#x2014;O&#x2014;, phenoxy or trichloromethoxy if X is oxygen; reacting the so obtained product of formula (XII) wherein X is oxygen or sulfur; Ris chloro if X is oxygen or sulfur; or Ris C-Calkoxy, CH&#x2014;C(&#x2550;CH)&#x2014;O&#x2014;, phenoxy or trichloromethoxy if X is oxygen; with the compound of formula (IX). 

Growing community of inventors

Munchwilen, Switzerland

Miroslav Terinek