HRP20191837T1 - Postupak za pripremu 5-fluoro-1h-pirazola počevši od heksafluoropropena - Google Patents

Postupak za pripremu 5-fluoro-1h-pirazola počevši od heksafluoropropena Download PDF

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HRP20191837T1
HRP20191837T1 HRP20191837TT HRP20191837T HRP20191837T1 HR P20191837 T1 HRP20191837 T1 HR P20191837T1 HR P20191837T T HRP20191837T T HR P20191837TT HR P20191837 T HRP20191837 T HR P20191837T HR P20191837 T1 HRP20191837 T1 HR P20191837T1
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chlorine
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Sergii Pazenok
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Bayer Animal Health Gmbh
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/16—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
    • C07C17/358—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by isomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (15)

1. Postupak za sintezu 5-fluoro-1H-pirazola s općom formulom (I) pri čemu R1 predstavlja (C1-C4)-alkil; naznačen time što sadrži korake - reakciju međuprodukta (3) s (C1-C4)-alkil-CONHNH2 da se dobije 3-perfluoroetil-4-perfluorometil-5-fluoro-pirazol (međuprodukt (4)) i - reakciju međuprodukta (4) sa (C1-C4)-alkilacijskim sredstvom, poželjno metilacijskim sredstvom radi dobivanja spoja formule (I) (ovdje se naziva korak 4).
2. Postupak za sintezu 5-fluoro-1H-pirazola s općom formulom (I) prema zahtjevu 1 naznačen time što sadrži korake - reakciju heksafluoropropena (međuprodukt (1)) u prisutnosti katalizatora da bi nastao njegov dimer perfluoro-4-metil-2-penten (međuprodukt (2)) i - izomerizaciju perfluoro-4-metil-2-pentena u perfluoro-2-metil-2-pentena (međuprodukt (3)) i - reakciju spoja (3) s (C1-C4)-alkil-CONHNH2 da se dobije 3-perfluoroetil-4-perfluorometil-5-fluoro-pirazol (međuprodukt (4)) i - reakciju međuprodukta (4) sa (C1-C4)-alkilacijskim sredstvom, poželjno metilacijskim sredstvom radi dobivanja spoja formule (I).
3. Postupak za pripravu spoja formule (IV) u kojoj R1 je C1-C4-alkil; i A1 je C-R2; i R2 je vodik, fluor, klor, brom, CN, NO2, po izboru halogenirani C1-C6-alkil, po izboru halogenirani C1-C4-alkoksi, po izboru halogenirani C1-C4-alkilsulfonil, po izboru halogenirani C1-C4-alkilsulfinil ili N-ciklopropilaminokarbonil (-C(=O)-NH-ciklopropil); poželjno vodik, fluor, klor, brom, CN, NO2, metil, etil, fluorometil, difluorometil, trifluorometil, 2,2,2-trifluoroetil, metoksi, etoksi, n-propoksi, 1 -metiletoksi, fluorometoksi, difluorometoksi, klorodifluorometoksi, diklorofluorometoksi, trifluorometoksi, 2,2,2-trifluoroetoksi, 2-kloro-2,2-difluoroetoksi, pentafluoroetoksi, metilsulfonil, metilsulfinil, trifluorometilsulfonil, trifluorometilsulfinil ili N-ciklopropilaminokarbonil, poželjnije vodik, fluor, klor, brom, CN, NO2, metil, fluorometil, difluorometil, trifluorometil, 2,2,2-trifluoroetil, metoksi, etoksi, ili pentafluoroetoksi, poželjno vodik, fluor, klor, brom, najpoželjnije klor; i A2 je C-R3 ili dušik; i R3 je vodik, metil, fluor ili klor, poželjno vodik; i T predstavlja jednu od skupina T1-T9 navedenih u nastavku, gdje je veza na glavnu skupinu pirazola označena zvjezdicom *,
ili *-C(=O)-NH- T9 ; i R6 neovisno jedan od drugoga predstavlja halogen, cijano, nitro, amino ili po izboru supstituiran C1-C6-alkil, C1-C6-alkiloksi, C1-C6-alkilkarbonil, C1-C6-alkilsulfanil, C1-C6-alkilsulfinil, C1-C6-alkilsulfonil, i n predstavlja vrijednosti 0-2, poželjno 0, uz uvjet da n je 0 ili 1in T5, T6 i T8 i uz uvjet da n je 0 u T7; i Q je vodik, cijano, hidroksi, formil ili jedna od skupina C1-C6-alkil, C3-C6-alkenil, C3-C6-alkynil, C3-C9-cikloalkil, C3-C9-heterocikloalkil, C1-C4-alkoksi, C4-C15-alkilcikloalkil, C4-C15-cikloalkilalkil, C1-C6-hidroksialkil, C6-aril-C1-C3-alkil, C5-C6-heteroaril-C1-C3-alkil, C1-C4-aminoalkil, aminokarbonil-C1-C4-alkil ili C1-C4-alkilamino-C1-C4-alkil koji su po izboru supstituirani s jednim, dva, tri, četiri ili pet, poželjno s jednim ili dva, poželjnije s jednim, supstituenata neovisno odabranim iz skupine koja sadrži hidroksi, nitro, amino, halogen, C1-C3-alkoksi, cijano, hidroksikarbonil, C1-C4-alkoksikarbonil, C1-C4-alkilkarbamoil, C4-C6-cikloalkilkarbamoil i po izboru neovisno s jednim, dva ili tri supstituenta odabranim iz skupine koja sadrži halogen, cijano, nitro, hidroksikarbonil, C1-C2-alkilkarbamoil, C1-C2-alkil, halogenirani C1-C2-alkil i C1-C2-alkoksi supstituirani fenil; poželjno Q je C3-C6-cikloalkil, ili C3-C6-cikloalkil koji je supstituiran s barem jednim supstituentom odabranim iz skupine koja sadrži klor, fluor, brom, jod, cijano i hidroksi, ili C6-aril-C1-C3-alkil; poželjnije ciklopropil, 1-cijano-ciklopropil ili benzil (-CH2-C6H5); naznačen time što sadrži korake prema zahtjevu 1 ili zahtjevu 2.
4. Postupak prema zahtjevu 3, naznačen time što spoj s formulom (IV) je spoj s formulom (II) pri čemu, R1, A1, R2, A2, R3 i Q su kako je definirano u zahtjevu 3, poželjno s formulom (II') pri čemu, A1, R2, A2, R3 i Q su kako je definirano u ovom zahtjevu za spojeve s formulom (II).
5. Postupak prema bilo kojem od patentnih zahtjeva 3 do 4, naznačen time što spoj s formulom (IV) je spoj (IIa)
6. Postupak prema bilo kojem od patentnih zahtjeva 3 do 5, naznačen time što nadalje obuhvaća korake: - reakciju spoja (I) s cijano-donorom da se dobije međuprodukt s formulom (6) pri čemu R1 je (C1-C4)-alkil; i - reakciju spoja (6) s anorganskom jakom bazom u prvom koraku hidrolize nakon čega slijedi dodavanje anorganske kiseline u drugom koraku hidrolize radi pripreme međuprodukta s formulom (7) pri čemu R1 je (C1-C4)-alkil; i - reakciju spoja s formulom (8) ili njegove soli (8') s aktiviranim oblikom (7') spoja (7) pri čemu R1, A1, A2, i Q su kako je definirano u zahtjevu 3 i LG je bilo koja odlazeća skupina, da se dobije spoj s formulom (II).
7. Postupak prema zahtjevu 3, naznačen time što spoj s formulom (IV) je spoj s formulom (III) u kojoj R1 je (C1-C4)-alkil; i A1 je C-R2; R2 je vodik, fluor, klor, brom, CN, NO2, po izboru halogenirani C1-C6-alkil, po izboru halogenirani C1-C4-alkoksi, po izboru halogenirani C1-C4-alkilsulfonil, po izboru halogenirani C1-C4-alkilsulfinil ili N-ciklopropilaminokarbonil (-C(=O)-NH-ciklopropil) ; poželjno vodik, fluor, klor, brom, CN, NO2, metil, etil, fluorometil, difluorometil, trifluorometil, 2,2,2-trifluoroetil, metoksi, etoksi, n-propoksi, 1 -metiletoksi, fluorometoksi, difluorometoksi, klorodifluorometoksi, diklorofluorometoksi, trifluorometoksi, 2,2,2-trifluoroetoksi, 2-kloro-2,2-difluoroetoksi, pentafluoroetoksi, metilsulfonil, metilsulfinil, trifluorometilsulfonil, trifluorometilsulfinil ili N-ciklopropilaminokarbonil, poželjnije vodik, fluor, klor, brom, CN, NO2, metil, fluorometil, difluorometil, trifluorometil, 2,2,2-trifluoroetil, metoksi, etoksi, ili pentafluoroetoksi, poželjno vodik, fluor, klor, brom, najpoželjnije klor; i A2 je C-R3 ili dušik; R3 je vodik, metil, fluor ili klor, poželjno vodik; i Q je vodik, cijano, hidroksi, formil ili jedna od skupina C1-C6-alkil, C3-C6-alkenil, C3-C6-alkynil, C3-C9-cikloalkil, C3-C9-heterocikloalkil, C1-C4-alkoksi, C4-C15-alkilcikloalkil, C4-C15-cikloalkilalkil, C1-C6-hidroksialkil, C6-aril-C1-C3-alkil, C5-C6-heteroaril-C1-C3-alkil, C1-C4-aminoalkil, aminokarbonil-C1-C4-alkil ili C1-C4-alkil-amino-C1-C4-alkil koji su po izboru supstituirani s jednim, dva, tri, četiri ili pet, poželjno s jednim ili dva, poželjnije s jednim, supstituenata neovisno odabranim iz skupine koja sadrži hidroksi, nitro, amino, halogen, C1-C3-alkoksi, cijano, hidroksikarbonil, C1-C4-alkoksikarbonil, C1-C4-alkilkarbamoil, C4-C6-cikloalkilkarbamoil i po izboru neovisno s jednim, dva ili tri supstituenta odabranim iz skupine koja sadrži halogen, cijano, nitro, hidroksikarbonil, C1-C2-alkilkarbamoil, C1-C2-alkil, halogenirani C1-C2-alkil i C1-C2-alkoksi supstituirani fenil; poželjno Q je C3-C6-cikloalkil, ili C3-C6-cikloalkil koji je supstituiran s barem jednim supstituentom odabranim iz skupine koja sadrži klor, fluor, brom, jod, cijano i hidroksi, ili C6-aril-C1-C3-alkil; poželjnije ciklopropil, 1-cijano-ciklopropil ili benzil (-CH2-C6H5); T predstavlja jedan od 5-eročlanih heteroaromatika T1-T8 navedenih u nastavku, gdje je veza na glavnu skupinu pirazola označena zvjezdicom *,
pri čemu R6 neovisno jedan od drugoga predstavlja halogen, cijano, nitro, amino ili po izboru supstituiran C1-C6-alkil, C1-C6-alkiloksi, C1-C6-alkilkarbonil, C1-C6-alkilsulfanil, C1-C6-alkilsulfinil, C1-C6-alkilsulfonil, i n predstavlja vrijednosti 0-2, poželjno 0, uz uvjet da n je 0 ili 1 u T5, T6 i T8 i uz uvjet da n je 0 u T7.
8. Postupak prema zahtjevu 7, naznačen time što spoj s formulom (III) je spoj s formulom (III') poželjnije spoj (IIIa) ili spoj (IIIb), koji je spoj s formulom (III"') pri čemu n je 0, A1 predstavlja C-Cl, A2 predstavlja C-H i Q predstavlja cijanociklopropil.
9. Postupak prema bilo kojem od patentnih zahtjeva 7 ili 8, koji obuhvaća Korake 1 do 4 kako je opisano u zahtjevu 2 i naznačen time što nadalje obuhvaća korake - reakciju spoja s formulom (I) s međuproduktom s formulom (11) nukleofilnom supstitucijom fluorida na položaju prstena spoja s formulom (I) (ovdje se naziva korak 9) pri čemu R1 je po izboru halogenirani (C1-C4)-alkil ili po izboru halogenirani ciklopropil; i U predstavlja brom, jod, triflat, boronsku kiselinu, boronski ester ili trifluoroboronat; i peteročlani cikli od E1-E3, ugljik i dušik predstavljaju 5-eročlane heterocikle odabrane iz skupine koja sadrži
pri čemu R6 neovisno jedan od drugoga predstavlja halogen, cijano, nitro, amino ili po izboru supstituiran C1-C6-alkil, C1-C6-alkiloksi, C1-C6-alkilkarbonil, C1-C6-alkilsulfanil, C1-C6-alkilsulfinil, C1-C6-alkilsulfonil, i n predstavlja vrijednosti 0-2, poželjno 0, uz uvjet da n je 0 ili 1 u T5, T6 i T8 i uz uvjet da n je 0 u T7; da se dobije međuprodukt s formulom (12); i - reakciju spoja s formulom (12) i spoja s formulom (13) (ovdje se naziva korak 10) pri čemu R1, A1, A2, i Q su kako je definirano za spoj s formulom (III) i U predstavlja brom, jod, triflat, boronsku kiselinu, boronski ester ili trifluoroboronat; i peteročlani cikli od E1-E3, ugljik i dušik predstavljaju 5-eročlane heterocikle odabrane iz skupine koja sadrži
pri čemu R6 neovisno jedan od drugoga predstavlja halogen, cijano, nitro, amino ili po izboru supstituiran C1-C6-alkil, C1-C6-alkiloksi, C1-C6-alkilkarbonil, C1-C6-alkilsulfanil, C1-C6-alkilsulfinil, C1-C6-alkilsulfonil, i n predstavlja vrijednosti 0-2, poželjno 0, uz uvjet da n je 0 ili 1 u T5, T6 i T8 i uz uvjet da n je 0 u T7; i M predstavlja brom, jod ili triflat kada U predstavlja boronsku kiselinu, boronski ester ili trifluoroboronat; ili M predstavlja boronsku kiselinu, boronski ester ili trifluoroboronat kada U predstavlja brom, jod ili triflat da se dobije spoj s formulom (III).
10. Postupak prema zahtjevu 3, naznačen time što spoj s formulom (IV) je spoj s formulom (III") poželjno s formulom (III''')
11. Postupak prema patentnom zahtjevu 10, naznačen time što sadrži korake prema zahtjevu 1 ili zahtjevu 2, ili po izboru nadalje obuhvaća korake kako je opisano u zahtjevu 9; ili po izboru nadalje obuhvaća korake - reakciju spoja s formulom (I) i azidnim-donorom da se dobije međuprodukt (14) pri čemu R1 je kako je definirano za spoj s formulom (III); i - reakciju međuprodukta (14) s međuproduktom s formulom (15) da se dobije međuprodukt (III"*) (ovdje se naziva korak 12) pri čemu R1, R6, A1, i A2 su kako je definirano za spoj (III), n je 0 ili 1 i PG je bilo koja zaštitna skupina karboksilne skupine kao što je C1-C6-alkil (npr., metil).
12. Postupak prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time što R1 je metil.
13. Postupak prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time što se koraci 3 i 4 provode u istom otapalu, poželjno acetonitrilu ili metilen kloridu, poželjnije metilen kloridu.
14. Postupak prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time što se koraci 3 i 4 provode u istom otapalu odabranom iz skupine koja sadrži acetonitril ili metilen klorid.
15. Upotreba međuprodukta (4) naznačena time što je za priređivanje spoja odabranog iz skupine koja sadrži spoj s formulom (I), (6), (7), (II), (IIa), (III), (III'), (IIIa), (III"), (III'''), (IIIb), i (IV), koji spojevi su svi kako je definirano u bilo kojem od prethodnih patentnih zahtjeva, i upotreba međuprodukta (4) za priređivanje N-metil-3-pentafluoroetil-4-trifluorometil-5-fluoro-pirazola (Ia), spoja s formulom (6a) i spoja s formulom (7a).
HRP20191837TT 2014-08-19 2019-10-10 Postupak za pripremu 5-fluoro-1h-pirazola počevši od heksafluoropropena HRP20191837T1 (hr)

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EP14181402 2014-08-19
PCT/EP2015/068782 WO2016026789A1 (en) 2014-08-19 2015-08-14 Process for the preparation of 5-fluoro-1h-pyrazoles starting from hexafluoropropene
EP15756864.3A EP3183237B1 (en) 2014-08-19 2015-08-14 Process for the preparation of 5-fluoro-1h-pyrazoles starting from hexafluoropropene

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US (1) US10059673B2 (hr)
EP (1) EP3183237B1 (hr)
JP (1) JP6676038B2 (hr)
KR (1) KR102540220B1 (hr)
CN (1) CN107108516A (hr)
AU (1) AU2015306261B2 (hr)
DK (1) DK3183237T3 (hr)
ES (1) ES2750353T3 (hr)
HR (1) HRP20191837T1 (hr)
HU (1) HUE045718T2 (hr)
IL (1) IL250441B (hr)
LT (1) LT3183237T (hr)
MX (1) MX369501B (hr)
PL (1) PL3183237T3 (hr)
PT (1) PT3183237T (hr)
SI (1) SI3183237T1 (hr)
TW (1) TW201619139A (hr)
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