Patent EA-001777-B1 (EA)
Title: Process for preparing 5-amino-1aryl-3-cyanopyrazole derivatives and intermediates used therefor
Inventor: D SILVA THEMISTOCLES
IPC: C07D231/38
Filed: 1998-02-25
Abstract: 1. A process for the preparation of a compound of formula (I):   wherein W is nitrogen or -CR4 ; R2, R4, R5 and R6 are independently selected from hydrogen, halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, R7S(O)n --, nitro, cyano and -SF5 ; R3 is hydrogen, halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, R7S(O)n --, nitro, cyano, --SF5, or phenyl substituted by one to five members of the group consisting of halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, R7S(O)n --, nitro, cyano and -SF5, which are the same or different; R7 is C1-6 alkyl or C1-6 haloalkyl; and n is 0,1 or 2; which comprises cyclizing, in the presence of a base, a compound of formula (II):   wherein W, R2, R3, R5 and R6 are as defined above. 2. A process according to claim 1, wherein the molar ratio of base to compound of formula (II) is from about 1:10 to about 10:1. 3. A compound of formula (II):   wherein W, R2, R3, R5 and R6 are as defined in Claim 1. 4. A compound according to Claim 3 wherein  R2 is halogen or hydrogen; R3 represents halogen, C1-6 haloalkyl, C1-6 haloalkoxy, R7S(O)p-, -SF5, or phenyl substituted by one to three members of the group consisting of trifluoromethyl, trifluoromethoxy, difluoromethyl, -S(O)nCr3, dichlorofluoromethyl, chlorodifluoromethyl, chlorodifluoromethoxy, dichlorofluoromethoxy and halogen. which may be the same or different; R4 is halogen; R5 and R6 are hydrogen. 5. A process far the preparation of a compound of formula (II) as defined in Claim 3, said process comprising the oxidation of a compound of formula (III):   wherein W, R2, R3, R5 and R6 are as defined in Claim 3, using an oxidant. 6. A process according to Claim 5 in which the oxidant is selected from a quinone; a peroxide; a hypohalite; an alkali metal hydroxide in the presence of air; a metal salt and a metal oxide. 7. A process for the preparation of a compound of formula (II) as defined in Claim 3, said process comprising the reaction of an enolate salt of a compound of formula (IV):   with a diazonium salt having the formula (V):   wherein W, R2, R3, R5 and R6 are as defined in Claim 3 and X is hydrogen sulphate or chloride. 8. A compound of formula (III):   wherein W, R2, R3, R5 and R6 are us defined in Claim 1. 9. A compound according to Claim 8 wherein  R2 is halogen or hydrogen; R3 represents halogen, C1-6 haloalkyl, C1-6 haloalkoxy, R7S(O)p-, -SF5, or phenyl substituted by one to three members of the group consisting of trifluoromethyl, trifluoromethoxy, difluoromethyl, -S(O)nCF3, dichlorofluoromethyl, chlorodifluoromethyl, chlorodifluoromethoxy, dichlorofluoromethoxy and halogen, which may be the same or different; R4 is halogen; R5 and R6 are hydrogen. 10. A process for the preparation of a compound of formula (III) as defined in Claim 8, said process comprising the reaction of an arylhydrazine having the formula (VII):   wherein W, R2, R3, R5 and R6 are as defined in Claim 8, with a compound of formula (VIII): CH(CN)=CH(CN)  (III)