OA11165A - Process for preparation of pyrazoloÄ4,3-dÜpyeimidin-7-ones and intermediates thereof - Google Patents

Claims (1)

1. 011165 -27- CLAIMS 1) A process for the préparation of a compound of formulae (IA) and (IB)

   O2S. O2S. 'N

   NCHc (IA) 'N (IB) NCH2CH3 comprising reacting a compound of formula (IIA) and (IIB) respectively in thepresence of "OR, wherein R in the case of formation of compound (IA) is CH2CH3and R in the case of formation of compound (IB) is CH2CH2CH3, where X is aleaving group: -28- 011165

   2) A process as claimed in claim 1 wherein X is selected from the groupconsisting of arylsuiphonyloxy, C1-C4 alkylsulphonyloxy, nitro or halosubstituted benzenesulphonyloxy, C1-C4 perfluoroalkylsulphonyloxy,optionally substituted aroyloxy, C1-C4 perfluoroalkanoyloxy, C1-C4alkanoyloxy, halo; diazonium; C1-C4 primary and secondary alkoxy, oxonium,perchloryloxy, quatenaryammonium C1-C4 alkylsulphonuloxy,halosulphonyloxy, halonium and diarylsulphonylamino. 3) A process as claimed in claim 2 wherein X is a halo or methoxy. 4) A process as claimed in claim 3 wherein X is fluoro, chloro or methoxy. 5) A process as claimed in claim 4 wherein X is fluoro or chloro. 6) A process as claimed in any one of the preceeding daims wherein OR is présent with an auxiliary base. 7) A process as claimed in claim 6 wherein the auxiliary base is selected fromthe group consisting of sterically hindered base , métal salts of 1-methylpiperazine (especially for compound IA), 1-ethylpiperazine (especially forcompound IB), morpholine ,a métal hydride, métal oxide, métal carbonateand métal bicarbonate. 8) A process as claimed in claim 7 wherein the sterically hindered base is amétal sait of a sterically hindered alcohol or amine. 9) A process as claimed in claim 8 wherein the métal sait of a stericallyhindered alcohol or amine is selected from the group consisting of a 011165 -29- secondary or tertiary C4-C12 alkanol, a C3-C12 cycloalkanol and a secondary ortertiary (C3-C3 cycloalkyl)Ci-C6 alkanol, a N-(secondary or tertiary C3-C6 alkyl)-N-(primary, secondary or tertiary Ο3-Οθ alkyl)amine, a N-(C3-C8 cycloalkyl)-N-(primary, secondary or tertiary O3-C6 alkyl)amine, a di(C3-C8 cycloalkyl)amine 5 or hexamethyldisilazane 1,5-diazabicyclo[4,3,0]non-5-ene 1,8- diazabicyclo[5,4,0]undec-7-ene and tertiary amines such as triethylamine. 10) A process as claimed in daims 9 wherein the auxiliary base is a métal sait ofa tertiary alkanol. 11) A process as claimed in any one of the preceding daims wherein the réaction 10 is carried out in an inert solvent or ROH or a mixture of both. 12) A process as claimed in daim 11 wherein the solvent is selected from the group consisting of éthanol (for IA), n-propanol (for IB), a secondary ortertiary C4-C12 alkanol, a C3-Ci2 cycloalkanol, a tertiary C4-C12 cycloalkanol, asecondary or tertiary (C3-C7 cycloalkyl)C2-C6 alkanol, a C3-C9 alkanone, 1,2- 15 dimethoxyethane, 1,2-diethoxyethane, diglyme, tetrahydrofuran, 1,4-dioxan, toluene, xylene, chlorobenzene, 1,2-dichlorobenzene, acetonitrile, dimethylsulphoxide, sulpholane, dimethylformamide, N-methylpyrrolidin-2-one,pyridine, and mixtures thereof. 13) A process as claimed in daim 12 wherein the solvent is selected from the 20 group consisting of éthanol (for IA), n-propanol (for IB), a tertiary C4-Ci2 alkanol, a tertiary C4-Ci2 cycloalkanol, a tertiary (C3-C7 cycloalkyl)C2-C6alkanol, a C3-C9 alkanone, 1,2-dimethoxyethane, 1,2-diethoxyethane,diglyme, tetrahydrofuran, 1,4-dioxan, toluene, xylene, chlorobenzene, 1,2-dichlorobenzene, acetonitrile, sulpholane, dimethylformamide, N- 25 methylpyrrolidin-2-one, pyridine, and mixtures thereof. 14) A process as claimed in daim 13 wherein the solvent is éthanol (for IA) orpropanol (for IB). 15) A process for the préparation of a compound of formula (IA) and (IB)according to any one of the preceding daims comprising reacting a 30 compound of formula (IIA) and (IlB) respectively with ZOR , or with ROH and 011165 -30- an auxiliary base as defined hereinbefore or with ZOR and an auxiliary base,wherein ZOR is a sait of OR and Z is a cation. 16) A process as claimed in claim 15 wherein compound (IA) is formed byreaction of compound (IlA): 5 a) with éthanol and auxiliary base, optionally in an inert solvent; or b) with ZOEt and an auxiliary base in éthanol or an inert solvent or both; or) c) with ZOEt and éthanol or an inert solvent or both. 17) A process as claimed in claim 15 wherein compound (IB) is formed byreaction of compound (IIB): 10 d) with propanol and auxiliary base, optionally in an inert solvent (as defined herebefore); or e) with ZOPr and an auxiliary base, in propanol or an inert solvent or both; or f) with ZOPr, and propanol or an inert solvent or both. 18) A process as claimed in any one of the preceding daims wherein the 15 compound of formula (HA) is prepared by coupling a compound of formula (VI IA)

   -31- 011165 with a compound of formula (IXA)

   (IXA) and a compound of formula (IIB) is prepared by coupling a compound of formula(VIIB)

   (VIIB) with a compound of formula (IXB)

   -32- 011165 19) A process as claimed in claim 18 wherein a compound of the formula (VllA) isformed by coupling a compound of formula (VIA) with N-methylpiperazine

   (VIA) and a compound of formula (VHB) is formed by coupling a compound of formula(VIA) with N-ethylpiperazine. 20) A compound of formula(IIA) and (IIB):

   wherein X is as defined in any one of daims 1 to 5. 21) A compound of formula (IlIA) and (IIIB): -33- 011165

   (HIA)

   wherein X is as defined in anyone of daims 1 to 5. 22) A compound of formula (VIIA) and (VIIB)

   (VIIB) wherein X is as defined in anyone of daims 1 to 5. 23) A compound as claimed in any of daims 20 to 22 herein X is selected from thegroup consisting of fluoro, chloro and methoxy.