LV10774B - Process for preparation of 6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid, 6-fluoro-4-oxo-7-(4-carbethoxy-1-piperazinyl)-1,4-dihydroquinoline-3-ethylcarboxylate and method for preparing thereof - Google Patents
Process for preparation of 6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid, 6-fluoro-4-oxo-7-(4-carbethoxy-1-piperazinyl)-1,4-dihydroquinoline-3-ethylcarboxylate and method for preparing thereof Download PDFInfo
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- LV10774B LV10774B LV930828A LV930828A LV10774B LV 10774 B LV10774 B LV 10774B LV 930828 A LV930828 A LV 930828A LV 930828 A LV930828 A LV 930828A LV 10774 B LV10774 B LV 10774B
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- piperazinyl
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- fluoro
- dihydroquinoline
- carboxylic acid
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Description
LV 10774LV 10774
CnOCOE ΠΟΠΥΗΕΗΜΡ l-3AMELL|EHHOl/l 6-ΦΤΟΡ-4-ΟΚΟΟ-7-/Ι-ΠΜΠΕΡΑ31/1Η1/1Π/4,4-ΑΜΓΜΑΡΟΧΙ/1ΗΟΠΜΗ-3-ΚΑΡΕΟΗΟΒΟΙ/1 Kl/ICnOTbl Μ CJ10>KHblM STMJIOBblI/l 3ΦΜΡ I-3AMEHEHHOI/1 6-ΦΤΟΡ'4-ΟΚΟΟ-7-/4-ΚΑΡΕ3ΤΟΚΟΜ-Ι-Π1/1ΠΕΡΑ3ΜΗΜΠ/-Ι,4-ΠΜΓΜΠΡΟΧΜΗΟΠΜΗ-3-ΚΑΡΕΟΗΟΒΟΙ/1 KMCflOTbl 1/1 CnOCOECnOCOE ΠΟΠΥΗΕΗΜΡ l-3AMELL | EHHOl / l 6-ΦΤΟΡ-4-ΟΚΟΟ-7- / Ι-ΠΜΠΕΡΑ31 / 1Η1 / 1Π / 4,4-ΑΜΓΜΑΡΟΧΙ / 1ΗΟΠΜΗ-3-ΚΑΡΕΟΗΟΒΟΙ / 1 Cl / ICnOTbl Μ CJ10 > KHblM STMJIOBblI / l 3ΦΜΡ I-3NAME / 1 6-ΦΤΟΡ'4-ΟΚΟΟ-7- / 4-ΚΑΡΕ3ΤΟΚΟΜ-Ι-Π1 / 1ΠΕΡΑ3ΜΗΜΠ / -Ι, 4-ΠΜΓΜΠΡΟΧΜΗΟΠΜΗ-3-ΚΑΡΕΟΗΟΒΟΙ / 1 KMCflOTbl 1/1 CnOCOE
ΕΓΟ ΠΟΠΥΗΕΗΙ/IRΕΓΟ ΠΟΠΥΗΕΗΙ / IR
HacTOflinee M3o6peieHne othocmtcji κ oGnacTM opraHunecKoro cnHTe3a n othocmtch κ cnoco6y nonyHeHHfl l-3aMemeHHoii 6-φτορ-4-οκοο-7-/Ι-nnnepa3MHMn/-lI4-fliirMflpoxMHonnH-3*Kap6oHOBoii κμοποτβι očmeM 0opwynbi I:HacTOflinee M3o6peieHne othocmtcji κ oGnacTM opraHunecKoro cnHTe3a n othocmtch κ cnoco6y nonyHeHHfl l-3aMemeHHoii 6-φτορ-4-οκοο-7 / Ι-nnnepa3MHMn / -lI4-fliirMflpoxMHonnH-3 * Kap6oHOBoii κμοποτβι očmeM 0opwynbi I:
rfle R «Bn^eTCfl CH2CH3l αμκποπροπμπομ, CH2CH2OH, CH2OCH2CH2OH, ηοβογο οποχηογο 30npa l-3aMemeHHOM 6-φτορ-4-οκοο-7-/4-κΒρ63τοκοΜ-Ι-nnnepa3MHnn/-l,4-flnrnnpoxnHonnH-3-Kap6oHOBOM KMcnoTbi φopMyπbι II: 0rfle R "Bn ^ eTCfl CH2CH3l αμκποπροπμπομ, CH2CH2OH, CH2OCH2CH2OH, ηοβογο οποχηογο 30npa l-3aMemeHHOM 6-φτορ-4-οκοο-7- / 4-κΒρ63τοκοΜ-Ι-nnnepa3MHnn / -l, 4-flnrnnpoxnHonnH-3-Kap6oHOBOM KMcnoTbi φopMyπbι II: 0
COOR1 COOCH2CH3 rfle R μμθθτ Te xe 3HaMeHM5i, hto m yKa3aHHbie paHee, a R1 αβπηθτοη stmhom, a Taxxe κ cnoco6y nonyHeHMfi coeflMHeHMfl φopMyπbl II, rfle R1 «BrifieTCfl BOflOpOflOM ΜΠΜ 3ΤΜΠ0Μ.COOR1 COOCH2CH3 rfle R μμθθτ Te xe 3HaMeHM5i, hto m yKa3aHHbie paHee, R1 αβπηθτοη stmhom, Taxxe κ cnoco6y nonyHeHMf coeflMHeHMfl φopMyπbl II, rfle R1 «BrifieTCfl BOflOpOflOM ΜΠΜ 3ΤΜΠ0Μ.
CoeflMHeHMe φopMyπbι I Mcnonb3yK>T b MeflMUMHe απη πθηθημα BOcnanMTenbHbix 3a6oneBaHMM. Ohm o6naflaioT ujmpokmm cneicrpoM aKTMBHocTeii προτΜΒ Kax rpaMnono>KMTenbHbix, TaK m rpaMOTpMqaTenbHbix čaKTepMM. -2 -CoeflMHeHMe φopMyðbι I Mcnonb3yK > T b MeflMUMHe απη πθηθημα BOcnanMTenbHbix 3a6oneBaHMM. Ohm o6naflaioT newer cneicrpoM aKTMBHocTeii προτΜΒ Kax rpaMnono > KMTenbHbix, TaK m rpaMOTpMqaTenbHbix čAKTepMM. -2 -
CymecTBOBana Heo6xoflHMocTb b hobom cnoco6e nonyHeHna coeflUHeHMfl φοριν^πω I, κοτορωρί 6bin 6bi caM no ce6e προοτ, οοθαιίηθημθ πθγκο 6bino 6bi Bbipen^Tb, c BbicoKMM BbixoflOM ueneBoro npoflyKTa, n stot cnoco6 βοπ>κθΗ 6bin 6bi omunaTbCJi ot yx<e 3aflBneHHbix cnoco6oB nonyHeHi/ifl yKa3aHHbix coeflUHeHnii. B naTeHTHoti nniepaiype pacKpbiT cnoco6 nonyHeHUfl οοθαηηθημα o6meii φopMyπbl I, HanpuMep, xax peaKLiM* xnop3aMeiueHHoro b ποποχθημμ 7- c nnnepa3HHOM b αποηοκομ naieHTHoii 3a?iBKe 66686/1979 n 33453/1980/ b Bbinox<eHHbix 3aflBKax ΦΡΓ flE 2840910 n 3308909, a Taoce xax peaxunfl rnAponn3a anKunoBoro οπο?κηογο 3φκρ3 b naTeHie Benbrnn 890223.CymecTBOBana Heo6xoflHMocTb b hobom cnoco6e nonyHeHna coeflUHeHMfl φοριν ^ πω I, κοτορωρί 6bin 6bi cam of ce6e προοτ, οοθαιίηθημθ πθγκο 6bino 6bi Bbipen ^ Tb, c BbicoKMM BbixoflOM ueneBoro npoflyKTa, n by learning cnoco6 βοπ > κθΗ 6bin 6bi omunaTbCJi ot yx < e 3aflBneHHbix cnoco6oB nonyHeHi / ifl yKa3aHHbix coeflUHeHnii. B naTeHTHoti nniepaiype pacKpbiT cnoco6 nonyHeHUfl οοθαηηθημα o6meii φopMyπbl I, Further preferably, XAX peaKLiM * xnop3aMeiueHHoro b ποποχθημμ 7- c nnnepa3HHOM b αποηοκομ naieHTHoii 3a? IBKe 66686/1979 n 33453/1980 / b Bbinox < eHHbix 3aflBKax ΦΡΓ FLE 2,840,910 3,308,909 n, a Taoce xax peaxunfl rnAponn3a anKunoBoro οπο? κηογο 3φκρ3 b naTeHie Benbrnn 890223.
Cnoco6 HacTOfliuero μ3ο6ρθτθημη ocymecTBnaioT τθκμμ o6pa30M, hto l-3aMeiueHHyio 6^Top-4-oKco-7-/4-Kap6o3TOKcn-l-nnnepa3HHnn/-l,4-Cnoco6 HacTOfliuero μ3ο6ρθτθημη ocymecTBnaioT τθκμμ o6pa30M, hto 1-3aMeiueHHylo 6 ^ Top-4-Co-7- (4-Kap6o3-Toccn-1-naphthalene3HHnn / -1, 4-
Anri/iApoxnHonnH-3-Kap6oHOByio KMcnoTy nnn ee cno>KHbifi sTunoBbitf 3φΐ/ΐρ očiueii φοριν^Γ^ι II:Anri / iApoxnHonnH-3-Kap6oHOByio KMcnoTy nnn ee cno > KHbifi sTunoBbitf 3φΐ / ΐρ očiueii φοριν ^ Γ ^ ι II:
OO
COOCH2CH3 γαθ R μμθθτ yKa3aHHbie paHee 3HaHeHMfl, a R1 αβπαθτοα boaopoaom nnn 3TnnoM, rnAponn3yioT b LuenoHHoii cpeAe ao nonyHeHnyi οοθακηθημα φορΜνπω I. ΓHAP0J1H3 npeAnoHTUTenbHo BeAyT b pacTBope KOH nnn aOH, m ripu TeMnepaType κμπθημα c očpambiM xonoAnnbHHKOM peaKLinoHHoii CMecn. rionyHeHHyK3 l-3aMeiueHHyio-6^Top-4-OKCo-7-/l-nMnepa3HHnn/-l,4-AnrnAPoxnHonnH-3-Kap6oHOByio Kncnoiy b φορΜθ conu HeūTpann3yioT, a 3aTeM nepeKpncTannn30BbiBai0T, HanpuMep, H3 cMecu Ν,Ν—ΑΜΜΘΤΙ/1ΠφθρΜ3ΜΙ/1ΑΘ m STaHona.COOCH2CH3 γαθ R μμθθτ yKa3aHHbie paHee 3HaHeHMfl a R1 αβπαθτοα boaopoaom nnn 3TnnoM, rnAponn3yioT b LuenoHHoii cpeAe ao nonyHeHnyi οοθακηθημα φορΜνπω I. ΓHAP0J1H3 npeAnoHTUTenbHo BeAyT b A solution of KOH nnn AOH, m dial TeMnepaType κμπθημα c očpambiM xonoAnnbHHKOM peaKLinoHHoii CMecn. rionyHeHHyK3-3aMeueHHyloxy-6-Top-4-OKCo-7- / 1-nnnep3HHnn / 1, 4-AnrnAPoxnHonnH-3-Kap6oHobyioccu conu HeuTpann3yioT, 3aTeM nepeKpncTannn30BbiBai0T, HanpuMep, H3 cMecu Ν, Ν / / 1ΠφθρΜ3ΜΙ / 1ΑΘ m STaHona.
CoeAMHeHne φοριν^/^ι II, γαθ R1 αβπαθτοα stuhom, flBnaeTc* hobhm οοθα^ηθημθμ, m TaK>Ke ηβπαθτοα oahum H3 očteKTOB HacTOJuiļero n3o6peTeHna. HoBbiM sinnoBbiii cno>KHbiii 3φκρ nonynaK)T cnocočoM, KOTopbiii TaioKe ηβπαθτοα oahmm W3 ο61>θκτοβ Hacroflmero μ3ο6ρθτθημη, H3 3TnnoBoro cnox<Horo 3φι/ιρ3 l-3aMeiueHHoii 6-Φτορ-7-γ3πομα-4-οκοο-Ι,4-αιί™αροχμηοπμη- -3- LV 10774 3-Kap6oHOBoii KUcnoTbi. CoeflUHeHne φορινιγπΝ II, b κοτοροΜ R1 nenneTcn BOflopoflOM, nonyHaK)T τ3κ>κθ M3 l-3aMeLAeHHon-6^Top-7-ranonA-4-oKco-l,4-AnrnflpoxnHonnH-3-Kap6oHOBoii KMcnoTbi, hto BMflHo H3 npnB6ABHHon Aanee cxeMbi peaKijnn:CoeAMHeHne /οριν ^ / ^ ι II, γαθ R1 αβπαθτοα stuhom, flBnaeTc * hobhm οοθα ^ ηθημθμ, mck ηβπαθτοα oahum H3 očteKTOB HacTOJuero n3o6peTeHna. Hobbs sinnoBbiii CNO > KHbiii 3φκρ nonynaK) T cnocočoM, KOTopbiii TaioKe ηβπαθτοα oahmm W3 ο61 > θκτοβ Hacroflmero μ3ο6ρθτθημη, H3 3TnnoBoro cNOx < Horo 3φι / ιρ3 l-3aMeiueHHoii 6-Φτορ-7-γ3πομα-4-οκοο-Ι, 4-αιί ™ αροχμηοπμη- -3- EN 10774 3-Kap6oHOBoii KUcnoTbi. CoefluheHne φορινιγπΝ II, b κοτοροΜ R1 nnNTcn BOflopoflOM, nonyHaK) T τ3κ > headKijnn:
base ▼base ▼
OO
COOR1COOR1
γαθ R = CH2CH3, UMKnonponi/inoM, CH2CH2OH, CH2OCH2CH2OH R1 = H, CH2CH3 X = TaKMM ranonAOM xax Cl, FγαθR = CH2CH3, UMKnonpone / inoM, CH2CH2OH, CH2OCH2CH2OH R1 = H, CH2CH3X = TaKMM ranonAOM xax Cl, F
PeaKUUto βθαυτ b ποπηρΗωχ opraHHHecKnx pacTBopnTenax μπμ nx CMecax, Τ3ΚΜΧ xax Ν,Ν-αμμθτμπΦορμθμμα, βι-ιθτοη nTpnn, nnpnAnH, 2-μθτκπ- 5-3TMnnHpHAHH, Ι-ΜΘΤΜΠΠΜρρΟΠΜΑΟΗ, ΑΜΜΘΤΜΠΟγΠΒφΟΚΟΜΑ H T. Α·, Β npncyTCTBHn areHTa, CBfl3biBa»omero o6pa3y»omyK>cfl HX. Οπη θτογο mojkho ncnonb30BaTb TaKoiži peareHT xax l-Kap6o3TOKcnnnnepa3HH oahh nnn KaKoe-nnčo Apyroe ocHOBaHi/ie, HanpuMep, KapčoHaT HaTpna nnn Kanna.PeaKUUto βθαυτ b ποπηρΗωχ opraHHHecKnx pacTBopnTenax μπμ nx CMecax, Τ3ΚΜΧ XAX Ν, Ν-αμμθτμπΦορμθμμα, βι-ιθτοη nTpnn, nnpnAnH, 2-μθτκπ- 5-3TMnnHpHAHH, Ι-ΜΘΤΜΠΠΜρρΟΠΜΑΟΗ, ΑΜΜΘΤΜΠΟγΠΒφΟΚΟΜΑ H T · Α, Β npncyTCTBHn areHTa, CBfl3biBa " omero o6pa3y »omyK > cfl HX. Οπη θτογο mojkho ncnonb30BaTb TaKoiži head-to-head xax l-Kap6o3TOKcnn Holiday3HH oahh nnn KaKoe-nnco Apyroe ocHOBaHi / ie, HanpuMep, KapčoHaT HaTpna nnn Apply.
Cnocoč HacTomuero n3o6peTeHna απα nonyHeHna οοθαμηθημμ φopMyπbι I aBnaeTca HOBbiM n ηθ onncaH b nnTepaiype. ΚροΜβ τογο, cnocoč nonyneHna n βηαθπθημα οοθαμηθημα φορινιγπΝ I προοτ, n npn stom AOCTnraKDT BblCOKHX BblXOAOB. flanee n3o6peieHne nnmocTpnpyeTca 6onee ποαρο6ηο cneAyK>mnMn npnMepaMn, KOTopbie, οαη3κο, ηθ οπθαυθτ paccMaipnBaTb xax orpaHHHntenbHbie. -4-Cnocoč HacTomato n3o6peTeHna απα nonyHeHna οοθαμηθημμ φopMyπbι I aBnaeTca HOBbiM n ηθ õncaH b nnTepaiype. ΚροΜβ τογο, cnocoč nonyneHna n βηαθπθημα οοθαμηθημα φορινιγπΝ I προοτ, n npn stom AOCTnraKDT BblCOKHX BblXOAOB. flanee n3o6peieHne nnmocTpnpyeTca 6onee ποαρο6ηο cneAyK > mnMn npnMepaMn, KOTopbie, οαη3κο, ηθ οπθαυθτ paccMaipnBaTb xax orpaHHHntenbHbie. -4-
llpuMep I l-3Tnn-6^Top-4-oKco-7-/l-nnnepa3HHnn/-l,4-flnrnflpoxMHonMH-3-11uMep I-3Tnn-6-Top-4-O-Co-7- [1-N-phthalene3HHnn / 1, 4-Fln-FlipoxMHonMH-3-
KapčoHOBa^ KucnoTa l-3TMn-6^Top-4-OKCO-7-/4-Kap63TOKCM-l-nnnepa3MHMn/-l14-flnrnflpoxnHonnH-3-Kap6oHOBoii KidcnoTbi cno>KHbiii STunoBbiii 3φΜρ (0,838 r, 0,002 μοπη) cycneHanpyKDT b cMecu 3TaHona (12 μπ) m 10% βοαηογο pacTBopa KOH (18 μπ) m HarpeBaiOT b τθηθημθ 10 Hacoe npn TeMnepaType ΚΜΠΘΗΜΛ C OČpaTHbIM XOnOflMnbHMKOM peaKLļMOHHOii CMecu (3a XOflOM peaKLinn cneflflT c noMOiubio τοηκοοιομηομ χροΜ3τοφ3φΜΐ/ι: Si02, 3TaHon: aMMnaK = 72 : 20). Ilocne 3aBepiueHMH peaKunn pacTBopmenb οτγοηπιοτ b Bai<yyMe, 15% HCI (15 μπ) nočaBnaioT, pacTBop (^MnbTpoBbiBaiOT, a 3aTeM pH pacTBopa ycTaHaBnnBaiOT 7 10% KOH. nonyHeHHbiū ocaaoK φnπbτpy^oτ, npoMbieaioT Bofloii m cywaT. ΠρΜ stom BbiflenaioT Ι-3ΤΜΠ-6-φτορ-4-οκοο-7-(Ι-nnnepa3HHnn)-l,4-flnrnflpoxMHonMH-3-Kap6oHOByto KMcnoTy (0,478 r, 75%), t. nnaBnemia 216-220°C.KapchoHOB? 3TaHona (12 μπ) m 10% βοαηογο solution of KOH (18 μπ) m HarpeBaiOT b τθηθημθ 10 HaCo npn TeMnepaType ΚΜΠΘΗΜΛ c OČpaTHbIM XOnOflMnbHMKOM peaKLļMOHHOii CMEC (3a XOflOM peaKLinn cneflflT c noMOiubio τοηκοοιομηομ χροΜ3τοφ3φΜΐ / ι: Si02, 3TaHon: aMMnaK = 72: 20 ). Ilocne 3aBepiueHMH peaKunn pacTBopmenb οτγοηπιοτ b Bai < yyMe 15% HCI (15 μπ) nočaBnaioT, solution was (^ MnbTpoBbiBaiOT, a 3aTeM pH solution of ycTaHaBnnBaiOT 7 10% KOH. NonyHeHHbiū ocaaoK φnπbτpy ^ oτ, npoMbieaioT Bofloii m cywaT. ΠρΜ stom BbiflenaioT Ι- 3ΤΜΠ-6-φτορ-4-οκοο-7- (Ι-nivala3HHnn) -1,4-flnflpoxMHonMH-3-Cap6oHOByt KMcnoTy (0.478 r, 75%), i.e. nnBnemia 216-220 ° C.
CneKTpanbHbie flaHHbie cooTBeTCTBy(OT nmepaTypHbiM aaHHbiM ΠρΜΜΘρ2 l-3TMn-6^Top-4-oKco-7-(l-nnnepa3HHnn/-1,4-flnrnflpoxMHonnH-3-CneKTpanbHbie flaHHbie cooTBeTCTBy (OT nmepTypHbiM aaHHbiM ΠρΜΜΘρ2-3TMn-6-Top-4-O-Co-7- (1-naphth3HHnn / -1,4-flnflpoxMHonnH-3-)
KapčoHOBan KucnoTa l-3Tnn-6^Top-4-oKco-7-/4-Kap6o3TOKCn-l-nnnepa3MHnn/-1,4-flnrnnpoxnHonnH-3-Kap6oHOByio xncnoTy (0,391 r, 0,001 μοππ) cycneHflnpyioT b CMecu STaHona (6 μπ) h 10% βοαηογο pacTBopa KOH (8 μπ), k HarpesatoT b TeMeHne 10 nacoB npn TeMnepaiype KuneHnn c očpambiM xonoannbHHKOM peaKLļnoHHoii cMecu (3a χοαομ peaKLinn cneaaT no aaHHbiM τοηκοοίομηομ χρ0Μ3Τ0Γρ3φΜΜ: Si02, 3TaHon: aMMuaK - 72:20). ilocne 3aBepiueHi/in peaKunn pacTBopmenb οτγοηπιοτ b BaKyyMe, aočaBnnioT 15% HCI (10 μπ), m MyTHbiū pacTBop φκπ^ρνιοτ m HeiiTpami3yK>T 10% KOH. rionyHeHHbiii ocaaoK φι^τρνιοτ c noacocoM, npoMbiBaKDT BOfloīi n cymaT. TaKMM očpa30M BblflenniOT Ι-3ΤΜΠ-6-φΤ0ρ-4-0Κ00-7-/Ι-ΠΜΠβρ33ΜΗΜΠ/-Ι,4-βΜΓΜηρ0ΧΜΗ0ΠΜΗ-3-Kap6oHOByto KucnoTy (0,240 r; 75%) t. nnaBneHUfl 216-220°C.KapčoHOBan KucnoTa-3Tnn-6 ^ Top-4-oCco-7- / 4-Kap6O3TOKCn-1-Neptune3MHnn / -1,4-fln-n-n-nnHonnH-3-Kap6O-Hocynyl (0.391 r, 0.001 μοππ) cycneHflnpyioT CMecu STaHona (6 μπ ) h 10% βοαηογο solution of KOH (8 μπ) k HarpesatoT b TeMeHne 10 nacoB npn TeMnepaiype KuneHnn c očpambiM xonoannbHHKOM peaKLļnoHHoii CMEC (3a χοαομ peaKLinn cneaaT of aaHHbiM τοηκοοίομηομ χρ0Μ3Τ0Γρ3φΜΜ: Si02, 3TaHon: aMMuaK - 72:20). ilocne 3aBepiueHi / in headThe pacTBopmenb οτγοηπιοτ b BaKyyMe, aočaBnnioT 15% HCl (10 μπ), m MyTHBi pacTBop φκπ ^ ρνιοτ m HeiiTpami3yK > T 10% KOH. rionyHeHHbiii ocaaoK φι ^ τρνιοτ c noacocoM, npoMbiBaKDT BOfloi n cymaT. TaKMM očpa30M BblflenniOT Ι-3ΤΜΠ-6-φΤ0ρ-4-0Κ00-7- / Ι-ΠΜΠβρ33ΜΗΜΠ / -Ι, 4-βΜΓΜηρ0ΧΜΗ0ΠΜΗ-3-Kap6oHOByt KucnoTy (0.240 r; 75%) t. nnaBneHUfl 216-220 ° C.
CneKTpanbHbie aaHHbie HaxoflflTcn b οοοτβθτοτβμμ c nnTepaTypHbiMM paHHblMU. -5- LV 10774 ΠρΜΜθρ 3 l-UMKnonponMn-6-0TOp-4-OKCO-7-/l-nnnepa3HHMn/-l14-flHrHflpOXHHOriMH-3-CneKTpanbHbie aaHHbie HaxoflflTcn b οοοτβθτοτβμμ c nnTepaTypHbiMM paHHblMU. -5- EN 10774 ΠρΜΜθρ 3 l-UMKnonponMn-6-OTOp-4-OKCO-7- / 1-naphtha3HHMn / -114-flHHFPOXHHOrMH-3-
KapčoHOBaa KucnoTa l-um<JionponMn-6-^Top-7-/4-Kap6o3TOKCM-l-nnnepa3MHMn/-4-oKco-l,4-flMrMflp0XMH0nMH-3-Kap60H0B0ii KMCnOTbl CnOJKHblti STMnOBbIM 3φΜρ ( 0,431 Γ, 0,001 μοππ) cycneHflnpyioT b siaHone (6 μπ) m 10% boahom pacTBope KOH (9 μπ), m HarpeBa»OT b τθηθημθ 8 nacoB npn TeMnepaType κμπθημπ c očpaTHbiM xonoflnnbHMKOM peaKUMOHHoti cMecM. 3aTeM pacTBopmenb οτγοηπιοτ b BaxyyMe κ cyxoMy ociaTKy AoāaBnnioT 5 μπ βοαν, μ pH ycTaHaBnnBaK)T I 15% BOflHbiM pacTBopoM HCI, MyTHbiti pacTBop φΐ/Η^τρνιοτ n HeūTpanM3y»OT 10% βοαηνμ pacTBopoM KOH no pH 7. l1onyHeHHbiii ocaAOK oτφnπbτpoBblBaιoτ, npoMbieaioT boaom w cymaT, rionyHaioT l-um<nonponnn-6-φΤθρ-4-ΟΚΟΟ-7-Ι-ΠΜΠβρ33ΜΗΜΠ/-Ι,4-ΑΜΓΜβρθΧΜΗΟΠΜΗ-3-Κ3ρ6θΗΟΒνΚ3 KMCnOTy (0,286 r, 86%), t. nnaBneHMfl 255-257°C. CneKTpanbHbie AaHHbie cooTBBTCTByioT nMTepaiypHbiM AaHHbiM.KapčoHOBaa KucnoTa 1 µm < JionponMn-6- ^ Top-7- / 4-Capo3TOKCM-1-Neptune3MHMn / -4-oCco-1, 4-flMrMflp0XMH0nMH-3-Kap60H0B0ii KMCnOTbl CnOJKHblt b siaHone (6 μπ) m 10% boahom pacTBope KOH (9 μπ), m HarpeBa »OT b τθηθημθ 8 nacoB npn TeMnepaType κμπθημπ c očpaTHbiM xonoflnnbHMKOM MAJOR HUMAN HMCMM. 3aTeM pacTBopmenb οτγοηπιοτ b BaxyyMe κ cyxoMy ociaTKy AoāaBnnioT 5 μπ βοαν, μ pH ycTaHaBnnBaK) TI 15% BOflHbiM pacTBopoM HCI, MyTHbiti solution was φΐ / ^ Η τρνιοτ n HeūTpanM3y "OT 10% βοαηνμ pacTBopoM KOH, pH 7 l1onyHeHHbiii ocaAOK oτφnπbτpoBblBaιoτ, npoMbieaioT boaom w cymaT, rionyHaiOt 1 µm < nonponnn-6-φΤθρ-4-ΟΚΟΟ-7-Ι-ΠΜΠβρ33ΜΗΜΠ / -Ι, 4-ΑΜΓΜβρθΧΜΗΟΠΜΗ-3-Κ3ρ6θΗΟΒνΚ3 KMCnOTy (0.286 r, 86%), t. nnaBneHMfl 255-257 ° C. CneKTpanbHbie AaHHbie cooTBBTCTByioT nMTepaiypHbiM AaHHbiM.
[IpuMep 4 l-/2-rnApoKCH3Tnn/-6^Top-4-oKco-7-/l-nnnepa3HHnn-l,4-[IpuMep 4,1- (2-rnApoKCH3Tnn / -6 ^ Top-4-Coco-7- [1-naphthalene3HHnn-1, 4-
AnrnApoxnHonnH-3-Kap6oHOBayi Kucnoia l-/2-rnAP0KCH3TMn/-6^T0p-4-0KC0-7-/4-Kap603T0KCH-l-nnnepa3HHMn/-l,4-AnrnApoxnHonnH-3-Kap6oHOByfo KHcnoiy (0,407 r, 0,001 μοππ) cycneHAnpyK)T b 3TaHone (6 μπ) h 10% boahom pacTBope KOH (9 μπ) h HarpeBaioT b τθηθημθ 14 nacoB m 45 MHHyT npn TeMnepaiype κμπθημπ c očpaTHbiM xonoAnnbHHKOM peaKunoHHOM cMecn. riocne 3aBepujeHnn peaKum/i pacTBopmenb οτγοηπιοτ b BaKyyMe, κ ocTan<y Ao6aBnntoT 5 μπ BOAbi n noAKucnnioT ao pH I I5% βοαηνμ pacTBopoM HCI. MyTHbiii pacTBop φι/^τρνιοτ, HeižiTpann3yiOT ao pH 7 10% βοαημμ pacTBopoM KOH, n nonyHeHHbiii ocaAOK οτφι/mbTpoBbiBaiOT. TaKUM o6pa30M nonyHaioT l-/2-rHAP0KCH3THn/-6^T0p-4-0KC0-7-/l-nMnepa3HHMn/-l,4-AMrMAP0XMH0nHH-3' Kap6oHOByio «ncnoTy (0,320 r, 96%), τ. ππθβπθηι/ιπ 6onee 300°C (nocne nepeKpncTannn3ai4HM H3 CMecu 3Τ3ηοπ-βοαα) · CneKTpanbHbie AaHHbie HaxoAHTcn b οοοτβθτοτβιιμ c nmepaTypHbiMH AaHHbiMH. flpuMep 5 - 6 -AnrnApoxnHonnH-3-Kap6oHOBayi Kucnoia 1- / 2-rnAP0KCH3TMn / -6? ) cycneHAnpyK) T b 3TaHone (6 μπ) h 10% boahom pacTBope KOH (9 μπ) h HarpeBaioT b τθηθημθ 14 nacoB m 45 MHHyT npn TeMnepaiype κμπθημπ c očpaTHbiM xonoAnnbHHKOM headKunoHHOM cMecn. riocne 3aBepujeHnn peaKum / i pacTBopmenb οτγοηπιοτ b BaKyyMe, κ ocTan < y Ao6aBnntoT 5 μπ BOAbi NON-BREAKING A pH I5% βοαηνμ pacTBopoM HCl. MyTHbiii pacTBop φι / ^ τρνιοτ, HeyTypeYyOn pH 7 10% βοαημμ pacTBopoM KOH, n nonyHeHHbiiiAaAOK οτφι / mbTpoBbiBaiOT. TaKum o6pa30M nonyHaioT1- / 2-rHAP0KCH3THn / -6 ^ T0p-4-0KC0-7- / 1-nMnepa3HHMn / 1, 4-AMrMAP0XMH0nHH-3'Cap6HOByOct (0.320r, 96%), τ. ππθβπθηι / ιπ 6onee 300 ° C (nocne nepeKpncTannn3ai4HM H3 CMecu 3Τ3ηοπ-βοαα) · CneKTpanbHbie AaHHbie HaxoAHTcn b οοοτβθτοτβιιμ c nmepaTypHbiMH AaHHbiMH. flpuMep 5 - 6 -
CnO>KHblM 3THnOBblK 3φκρ l-3THn-6^TOp-4-OKCO-7-/4-Kap603TOKCH-l-nnnepa3MHMn/-l ,4-ΑΜΓΜΑρθΧΜΗΟΠΜΗ-3-Κ3ρ6θΗΟΒΟΜ KMCnOTbl Ι-3Τ1/ΙΠ-6,7-βΜφΤθρ-4-ΟΚΟΟ-Ι,4-ΑΜΓΜΑρθΧΜΗΟΠΜΗ-3-Κ3ρ6θΗΟΒθίί KMCHOTbl cno>KHbiii STnnoBbin 3φκρ (0,562 r, 0,0020 Mona), l-Kap6o3TOKCnnnnepa3HH (0,348 r, 0,0022 Mona) n xap6oHaT Kanna (0,303 r, 0,0022 Mona) cycneHflnpyK)T b Ν,Ν-αμμθτμπΦορμ3μι^αθ (6 μπ) n HarpeBaiOT b τθηθηκθ 4 nacoB npn TeMnepaiype κιλπθημπ c očpaTHbiM χοποαμπβημκομ peaKunoHHon CMecn. 3a peaKunen cnenaT c noMombio τοΗκοοηοήΗοη χροΜ3τοφ3φΐΊΐ/ΐ (Si02; 3TaHon: aMMnaK 72 : 20). Ilocne OKOHnaHna peaKLinn pacTBopnTenb OTroHatOT b BaKyyMe, Ao6aBnaioT BOfly (20 μπ) n 3KCTparnpyioT χποροφορΜΟΜ. ΧηοροφορΜΟΒοή cnon cyiuaT, pacTBopmenb οτγόηπιοτ b BaKyyMe, cyxon ocTaTOK eme pa3 npoMbiBaioT boaom n nepeKpncTannn30BbiBatoT H3 STaHona. B pe3ynbTaTe BbiflenaioT l-3Tnn-6^Top-4-OKco-7-/4-Kap6o3TOKcn-l-nnnepa3HHnn/-l,4-AnrnflpoxnHonnH-3-Kap6oHOBoii KncnoTbi STnnoBbiii cno>KHbin 3φκρ (0,448 r, 53%), t. nnaBneHna 198-202°C.CnO > KHblM 3THnOBblK 3φκρ-3THn-6-TOp-4-OKCO-7- / 4-Kap603TOKCH-1-ene3MHMn / -1, 4-ΑΜΓΜΑρθΧΜΗΟΠΜΗ-3-Κ3ρ6θΗΟΒΟΜ KMCnOTbl Ι-3Τ1 / ΙΠ-6,7-βΜφΤθρ -4-ΟΚΟΟ-Ι, 4-ΑΜΓΜΑρθΧΜΗΟΠΜΗ-3-Κ3ρ6θΗΟΒθίί KMCHOTbl &nd; KHbiii STnnoBbin 3φκρ (0.562 r, 0.0020 Mona), 1-Kap6o3TOKCnn Holiday3HH (0.348 r, 0.0022 Mona) n xap6oHaT Can (0.303 r, 0 , 0022 Mona) cycneHflnpyK) T b Ν, Ν-αμμθτμπΦορμ3μι ^ αθ (6 μπ) n HarpeBaiOT b τθηθηκθ 4 nacoB npn TeMnepaiype κιλπθημπ c očpaTHbiM χοποαμπβημκομ headKunoHHon CMecn. 3a peaKunen cnenaT c noMombio τοΗκοοηοήΗοη χροΜ3τοφ3φΐΊΐ / ΐ (Si02; 3TaHon: AMMNK 72: 20). Ilocne OKOHnaHna headKLinn pacTBopnTenb OTroHatOT b BaKyyMe, Ao6aBnaioT BOfly (20 μπ )'s 3KCTparnpyioT χποροφορΜΟΜ. ΧηοροφορΜΟΒοή cnon cyiuaT, pacTBopmenb οτγόηπιοτ b BaKyyMe, cyxon ocTaTOK em3 npoMbiBaioT boaom n nepeKpncTannn30BbiBatoT H3 STaHona. B pe3ynbTaTe BbiflenaioT-3Tnn-6β-Top-4-OKco-7- / 4-Capo-3-Tocn-1-yn-3HHnn / 1, 4-AnrnflpoxnHonnH-3-Kap6O-HOBoii KncnoTbi STnnoBbiii > KHbin 3φκρ (0.448 r, 53%), t. nnaBneHna 198-202 ° C.
CneKTpanbHbie AanHbie: IH 9\MP (CflCI), TMC ): 5CH3= 1,20-1,33 μα (μ, 9H), 6H(nnnepa3HHnn) = 3,25 μα (μ, 4H), 3,67 μα (μ, 4H), 6CH2 = 4,00-4,60 μα (μ, 6H), 5Ha = 6,70 ma,CneKTpanbHbie AanHbie: IH 9 MP (CflCl), TMC): 5CH3 = 1.20-1.33 μα (μ, 9H), 6H (N, 3HHnn) = 3.25 μα (μ, 4H), 3.67 μα ( μ, 4H), 6CH2 = 4.00-4.60 μα (μ, 6H), 5Ha = 6.70 m
4yFH8 = 7 Γ14, IH δΗ5 = 7,95 μα (A, 3yFH5 = 13 Tu, IH), 5H2 = 8,32 ma (c, IH) 19F flMP (CflCl3, CCI3F): 6F =-123,00 ma (AA, \FHs = 13 Tu, 4yFH8 = 7 Tu)4yFH8 = 7Γ14, 1H δΗ5 = 7.95 μα (A, 3yFH5 = 13 Tu, 1H), 5H2 = 8.32 m (c, 1H) 19F flMP (CflCl3, CCl3F): 6F = -123.00 m AA, FHs = 13 Tu, 4yFH8 = 7 Tu)
SneMeHTHbiii aHann3: C21H26FN305SneMeHTHbii aHann3: C21H26FN3O5
PaccMnTaHo: % 419,185635PaccMnTaHo:% 419.185635
HaiiAeHo: 419,1853HaiiEeHo: 419.1853
Macc-cneicrp μ/θ: 420 (M+ + 1,4%, 419 (M+, 16%), 348 (20), 347 (100), 245 (8), 318 (9), 56 (27),32(12). flpnMep 6 -7- LV 10774 l-3Tnn-6^Top-4-oKco-7V4-Kap6o3TOKCM-l-nMnepa3HHM/i/-l,4-flnrnflpoxnHonnH-3-Kap6oHOBafl KMcnoTa Ι-3ΤΜΠ-6-φΤ0ρ-7-ΧΠ0ρ-4-0Κ00-Ι,4-ΑΜΓΜβρ0Χ11Η0ΠΜΗ-3-Κ3ρ60Η0ΒγΚ) ΚΜοηοτγ (0,270 r, 0,001 Morm) n l-Kap603T0Kcnnnnepa3MH (0,632 r, 0,004 μοπβ) cycneHflnpyK)T b 2-μθτμπ-5-3ΤΜΓιπμρι/1Αμηθ (4 μπ) μ I—ΜΘΤΜΠΠΜρροηΐ/ΐβΟΗΘ (2 μπ) n HarpeBaioT Β ΤΘΗΘΗΚΘ 4 HacoB πρι/ι TeMnepaType κι/ιπθημπ peaKUMOHHoCi CMecu c o6paTHbiM χοποαμπι=ημκομ. Ilocne 3aBepiueHHfl peaKLļm/i Ao6aBnyuoT 10 μπ xnopo<ļiopMa, pacTBop npoMbieaioT 10% βοαηνμ pacTBopoM HCI n nocne βτογο βοαομ ao HeMTpann3aunn pacTBopa. ΧποροφορΜΟΒΗϋ cnoPi cyiuaT, a pacTBopwenb οτγοηπκ)τ b BaKyyMe. Cyxoii paccbinnaTbiM ocrraTOK npoMbieaioT βτβηοπομ h cyujaT. TaKMM o6pa30M nonysaioT l-3Tnn-6^Top-7-/4-Kap6o3TOKcn/-l-nnnepa3HHnn/-4-oKco-l,4-flnrnflpoxnHonnH-3-Kap6oHOByio KncnoTy (0,195 r, 50%). T. nnaBnem/m 270-273°C.Macc-cneicrp μ / θ: 420 (M + 1.4%, 419 (M +, 16%), 348 (20), 347 (100), 245 (8), 318 (9), 56 (27), 32 (12) .fpnMep 6 -7-LV 10774-3Tnn-6 ^ Top-4-Coco-7V4-Kap6O3TOKCM-1-nMnepa3HHM / i / 1, 4-Fln-FlpoxnHonnH-3-Kap6oHOBafl KMcnoTa-3ΤΜΠ-6- φΤ0ρ-7-ΧΠ0ρ-4-0Κ00-Ι, 4-ΑΜΓΜβρ0Χ11Η0ΠΜΗ-3-Κ3ρ60Η0ΒγΚ) ΚΜοηοτγ (0,270 r, 0,001 Morm) n l-Kap603T0Kcnc3MH (0,632 r, 0,004 μοπβ) cycneHflnpyK) T b 2-μθτμπ-5-3ΤΜΓιπμρι / 1Αμηθ (4 μπ) μ I - ΜΘΤΜΠΠΜρροηΐ / ΐβΟΗΘ (2 μπ) n HarpeBaioT 4 HacoB πρι / ι TeMnepaType κι / ιπθημπ main KUMOHHoCi CMecu c o6paTHbiM χοποαμπι = ημκομ. Ilocne 3aBepiueHHfl MAIN CLIMATE / Ao6aBnyOnT 10 μπ xnopo < llm, pacTBop npoMiBiOiT 10% βοαηνμ pacTBopoM HCl βτογο βοαομ ao HeMTpann3aunn pacTBopa. ΧποροφορΜΟΒΗϋ cnoPi cyiuaT, pacTBopwenb οτγοηπκ) τ b BaKyyMe. Cyxoii paccbinnaTbiM ocrraTOK npoMbieaioT βτβηοπομ h cyujaT. TaKMM6pa30M nonysaioT-3Tnn-6 ^ Top-7- / 4-Kap6O3TOKcn / -1-n-n-3HHnn / -4-oCco-1,4-flnflpoxnHonnH-3-Kap6HOByio KncnoTy (0.195 r, 50%). T. nnaBnem / m 270-273 ° C.
CneKTpanbHbie Aam-ibie: IH PMP (CFgCOOH, TMC): δΟΗ3=1,42 μπ^ΘΛ Tu (t, 3H), 5CH3=1,78 Μβ (τ, γ=6,4 Γα, 3H), 6H(m/inepa3UHnn)=3,88 μα (μ, 8H), 5CH2=4,41 ma (kb, 6,4 Tu, 2H), 6CH2=4,84 μα (kb, γ=6,4 Tu, 2H), δΗ8 - 7,40 μα (A, 4yFH8=6,5 Tu, IH), δΗ5=8,27 μα (A, 3yFH5=13 Tu, IH), δΗ2=9,28 ma (c, IH). 19F flMP (CF3COOH, CCI3F): 5F=-112,07 ma (AA, 3yFH5=13 Tu, 4yFH8=6,5 Tu)CneKTpanbHbie Am-ibie: IH PMP (CFgCOOH, TMC): δΟΗ3 = 1.42 μπ ^ ΘΛ Tu (t, 3H), 5CH3 = 1.78 Μβ (τ, γ = 6.4 Γα, 3H), 6H (m / inepa3UHnn) = 3,88 μα (μ, 8H), 5CH2 = 4,41 ma (kb, 6,4 Tu, 2H), 6CH2 = 4,84 μα (kb, γ = 6,4 Tu, 2H), δΗ8 - 7.40 μα (A, 4yFH8 = 6.5 Tu, 1H), δΗ5 = 8.27 μα (A, 3yFH5 = 13 Tu, 1H), δΗ2 = 9.28 m (c, 1H). 19F flMP (CF3COOH, CCl3F): 5F = -112.07 ma (AA, 3yFH5 = 13 Tu, 4yFH8 = 6.5 Tu)
Macc-cneKTp M/e: 392 (M+ + 1,3%), 391 (M+, 15%), 348 (15), 347 (100), 151 (14), 83 (12), 56 (10), 44 (15), 43 (11).Macc-cneKTp M / e: 392 (M + 1.3%), 391 (M +, 15%), 348 (15), 347 (100), 151 (14), 83 (12), 56 (10), 44 (15), 43 (11).
SneMeHTHbiū aHann3 απα Ci9H22FN305 PaccHHTaHo: 391,154SneMeHTHbu aHann3 απα C19H22FN305 PaccHHTαHo: 391.154
HaCiAeHo: 391,154 -8- llpuMep 7HaCiAeHo: 391.154 -8
CnO>KHbin 3THnOBblŪ 3φΜρ Ι-ΜΜΚΠΟΠρθΠΜΠ-6-φΤθρ-7-/4-Κ3ρ6θ3ΤΟΚΟΜ-Ι-nnnepa3HHnn/-4-oKco-l,4-flnrnflpoxMHonnH-3-Kap6oHOBoii KncnoTbiCnO > KHbin 3THnOBblŪ 3φΜρ Ι-ΜΜΚΠΟΠρθΠΜΠ-6-φΤθρ-7- / 4-Κ3ρ6θ3ΤΟΚΟΜ-Ι-nivala3HHnn / -4-oCco-1, 4-flnflpoxMHonnH-3-Kap6oHOBoii KncnoTbi
Cno>KHbiii 3TnnoBbiii 3φι/ιρ Ι-141^ΚΠΟΠρθΠΜΠ-6,7-ΑΜφΤθρ-4-ΟΚΟΟ-Ι,4-flnrnflpoxnHonnH-3-Kap6oHOBoii KucnoTbi (0,439 r, 0,0015 Mona), l-Kap6o3TOKcnnunepa3HH (0,261 r, 0,00165 Mona) n KapčoHaT Kanna (0,228 r, 0,00165) cycneHflnpyK>T b Ν,Ν-ΑΜΜθτκπφορΜβΜΐ/ΐΑβ (5 μπ) n HarpeeaioT b TeHeHne 4 nacoB npn TeMnepaType KnneHna c očpaTHbiM xonoflnnbHHKOM peaKunoHHon CMecn. ilocne 3aBepweHnn peaKunn pacTBopmenb οτγοηλιοτ b BaKyyMe, Ao6aBna(OT 20 μπ eopbi n 3KCTparnpytoT χποροφορΜΟΜ. ΧποροφορΜΟΒΗή cnoii cyiuaT, n TBepayio nacTb οτγοη3ιοτ. Tbkum o6pa30M nonynaioT cnoKHbiii 3φΐΊρ STnnoBbiii Ι-ρηκποπροπηπ-6-φτορ-7-/4-κ3ρ6θ3Τθκοη-l-nnnepa3HHnn/-4-oKco-l,4-AnrnApoxnHonnH-3-Kap6oHOBoii KncnoTbi (0,529 r, 82%). nonyHeHHbin npoflyi<T nepeKpncTannn30BbiBaioT n3 siaHona, T.nnaBneHnn 225-229°C.Cn < + > KHbiii 3TnnoBbiii 3 < / RTI > 0,00165 Mona) n KapčoHaT Carry (0,228 r, 0,00165) cycneHflnpyK > T b Ν, Ν-ΑΜΜθτκπφορΜβΜΐ / ΐΑβ (5 μπ) n BleedingT bt teHeHne 4 nacoB npn TeMnepaType KnneHna c očpaTHbiM xonoflnnbHHKOM headKunoHHon CMecn. ilocne 3aBepweHnn peaKunn pacTBopmenb οτγοηλιοτ b BaKyyMe, Ao6aBna (OT 20 μπ eopbi n 3KCTparnpytoT χποροφορΜΟΜ. ΧποροφορΜΟΒΗή cnoii cyiuaT, n TBepayio nacTb οτγοη3ιοτ. Tbkum o6pa30M nonynaioT cnoKHbiii 3φΐΊρ STnnoBbiii Ι-ρηκποπροπηπ-6-φτορ-7- / 4-κ3ρ6θ3Τθκοη-l- nickel3HHn / -4-oCco-1,4-AnrnApoxnHonnH-3-Kap6oHoboii KncnoTbi (0.529 r, 82%) nonyHeHHbin nofofil < T nepeKpncTannn30BbiBaio n3 siaHona, T.nnaBneHnn 225-229 ° C.
CneicrpanbHbie AaHHbie IH flMP (CflCIgTMC): 5CH3, CH3H (unKnonponnn)=1,45 (μ, IOH), 5H(nnnepa3HHnn), H(unKnonponnn)=3,32 μα (μ, 5H), 3,73 μα (μ, 4H), 6CH2CH2=4,32 μα (μ, 4H), 6H8=7,20 μα (A, 4yFHa=6,4 Tu, IH), 6H5 - 7,87 ma (A,3yFH5=13ru, IH), 5H2 - 8,43 ma (c, IH). 19F<RMP(CF3COOH, CCI3F): 5F=-112,57 ma (flfl, 3yFH5=13 Tu, 4yFM8=6,5 Tu)Cneicrpanb Hbie AaHHbie 1H flMP (CflClgTMC): 5CH3, CH3H (unKnonponnn) = 1.45 (μ, IOH), 5H (n-3HHn), H (unKnonponnn) = 3.32 μα (μ, 5H), 3.73 μα (μ , 4H), 6CH2CH2 = 4.32 μα (μ, 4H), 6H8 = 7.20 μα (A, 4YFHa = 6.4 Tu, 1H), 6H5 - 7.87 ma (A, 3YFH5 = 13ru, 1H) , 5H2 - 8.43 m (c, 1H). 19F < RMP (CF3COOH, CCI3F): 5F = -112.57 ma (flfl, 3yFH5 = 13 Tu, 4yFM8 = 6.5 Tu)
Macc-cneKTp M/e: 432 (M+ + 1,6%), 431 (M+21%), 386 (8), 360 (21), 359 (100), 329 (6), 257 (6), 230 (6), 229 (5), 56 (26). ΠρΜΜβρ 8 l-UHKnonponnn-6^Top-7-/4-Kap6o3TOKCn-l-nnnepa3HHnn/-4-oKco-l,4-AnrnflpoxnHonnH-3-Kap6oHOBaa Kncncrra l-i4HKnonponnn-6,7-A^Top-4-OKCo-l,4-AnrnApoxnHonnH-3-Kap6oHOByio KncnoTy (0,265 r, 0,001 Mona), l-Kap6o3TOKCn-nnnepa3HH (0,174 r, -9- LV 10774 0,0011 μοππ) n KapčoHaT Kanna (0,152 r, 0,0011 Monen) cycneHflnpyioT b Ν,Ν—111ΊΜΘΤΙ/ΙΠφθρΜ3Μ11ΑΘ (10 ΜΠ) M HarpeBaiOT B ΤβΗβΗΙ/ΙΘ 2,5 MaCOB npn TeMnepaType KnneHna c o6paTHbiM xononnnbHHKOM peaKLinoHHon CMecn. ilocne 3aBepiueHna peaKunn pacTBopmenb οτγόηπιοτ b BaKyyMe, κ cyxoMy ocTaTKy AOČaBnaioT Bony (10 μπ), n pH cycneH3Hn ycTaHaBnnBafOT 15% HCI no HenTpanbHon. OcaflOK cm^nnbTpoBbiBaioT n cyiuaT. nonyMeHHbin npoAyKT nepeKpncTannn30BbiBaioT H3 ΑΜΜβτηπφορΜ3ΜηΑΒ. TaxnM o6pa30M nonyHatoT l-L4HKnonponnn-6^Top-7-/4-Kap6o3TOKCn-l-nnnepa3HHnn/-4-OKCo-l,4-flnrnApoxnHonnH-3-Kap6oHOByK) KHcnoTy (0,282 r, 70%), t. nnaBneHna 250°C. CneKTpanbHbie flaHHbie IH HMP (CF3COOH, TMC): 5CH3H (unKnonponnn)=1,50 ma/m, 7H/, 5H(nnnepa3HHnn), H(unKnonponnn)= 3,92 μα (μ, 9H), 5CH2=4,41 μα (κβ, γ=6,4 Γρ, 2H), δΗ8=7,88 μα (A, 4yFH8=6,5 Tu, IH), 5HS=8,27 ma (a, 3yFH5=13ru, IH), δΗ2= 9,32 (m.a. c, IH). 19 F 9\MP (CF3COOH, CFCI3): 5F=-112,40 μα (AA, 3yFH5=13 Tu, 4yFH8=6,5 Γρ)Macc-cneKTp M / e: 432 (M + + 1.6%), 431 (M + 21%), 386 (8), 360 (21), 359 (100), 329 (6), 257 (6), 230 (6), 229 (5), 56 (26). ΠρΜΜβρ 8-UHKnonponnn-6 ^ Top-7- / 4-Capo-3TOKCn-1-N-β-3HHn / -4-O-Co-1,4-AnrnflpoxnHonnH-3-Kap6HOBa Knccrra-I4HKnonponnn-6,7-A ^ Top-4- OKCo-1,4-AnrnApoxnHonnH-3-Kap6oHobyio KncnoTy (0.265 r, 0.001 Mona), 1-Kap6o3TOKCn-3HH (0.174 r, -9- LV 10774 0.0011 μοππ) n KapčoHaT Carrier (0.152 r, 0.0011 Multiple ) cycneHflnpyioT b Ν, ΊΜΘΤΙ-111ΊΜΘΤΙ / ΙΠφθρΜ3Μ11ΑΘ (10 ΜΠ) M HarpeBaiOT B ΤβΗβΗΙ / ΙΘ 2.5 MaCOB npn TeMnepaType KnneHna c o6paTHbiM xononnnbHHKOM headKLinoHHon CMecn. ilocne 3aBepiueHna headThe pacTBopmenb οτγόηπιοτ b BaKyyMe, κ cyxoMy ocTaTKy AOČaBnaioT Bony (10 μπ), n pH cycneH3Hn ycTaHaBnnBafOT 15% HCl from HenTpanbHon. OcaflOK cm ^ nnbTpoBbiBaioT n cyiuaT. nonyMeHHbin npoAyKT nepeKpncTannn30BbiBaioT H3 ΑΜΜβτηπφορΜ3ΜηΑΒ. TaxnMo6pa30M nonyHatoT1-L4HKnonponnn-6H-Top-7- / 4-Capo-3TOCCn-1-N-3HHNN-4-OKCo-1,4-flnApoxnHonnH-3-Kap6oHOByK) (0.282 r, 70%), t. nnaBneHna 250 ° C. CneKTpanb Hbie flaHHbie 1H HMP (CF3 COOH, TMC): 5CH3H (unKnonponnn) = 1.50 m / m, 7H /, 5H (nephalic3HHn), H (unKnonponnn) = 3.92 μα (μ, 9H), 5CH2 = 4.41 μα (κβ, γ = 6.4 Γρ, 2H), δΗ8 = 7.88 μα (A, 4yFH8 = 6.5 Tu, 1H), 5HS = 8.27 m (a, 3yFH5 = 13ru, 1H), δΗ2 = 9.32 (m, c, 1H). 19 F 9 MP (CF 3 COOH, CFCl 3): 5F = -112.40 μα (AA, 3YFH5 = 13 Tu, 4yFH8 = 6.5 Γρ)
Macc-cnetcrp M/e: 404 (M+ + 1,4%), 403 (M+, 21%), 360 (28), 359 (100), 347 (14), 289 (14), 287 (15), 257 (12), 245 (17), 57 (11), 56 (30), 44 (26). SneMeHTHbiii aHann3 αππ C2oHhhFN305 PaccnnTaHo: 403,154Maccnetcrp M / e: 404 (M + + 1.4%), 403 (M +, 21%), 360 (28), 359 (100), 347 (14), 289 (14), 287 (15), 257 (12), 245 (17), 57 (11), 56 (30), 44 (26). SneMeHTHbii aHann3 αππ C2HhhFN305 PaccnnTaHo: 403.154
HaiiAeHo: 403,150 npnMep 9 l-unKnonponnn-6^Top-7-/4-Kap6o3TOKCn-l-nnnepa3HHnn/-4-oKCO-l,4-AnrnApoxnHonnH-3-Kap6oHOBaa KncnoTa Ι-ΜΜΚΠΟΠρθΠΙ/1Π-6-φΤθρ-7-ΧΠθρ-4-ΟΚΟΟ-Ι,4-ΑΜΠ/1ΑρθΧΜΗΟΠΜΗ-3-Kap6oHOBy»o Kncnoiy (0,281 r, 0,001 μοππ) n l-Kap603T0Kcnnnnepa3nH (0,632 r, 0,004 Mona) cycneHAnpyraT b 2-MeTnn-5-3TnnnnpnAHHe (8 μπ) n 1-MeTnn-nnpponnAOHe (2 μπ) n HarpeeaiOT b Tenei-ine 4 sacoB npn TeMnepaiype κηπβΗηη c očpaTHbiM xonoAnnbHnKOM peaKunoHHon cMecn. Ilocne 3aBepiueHna peaKLjnn Ao6aBnaK)T 20 μπ χποροφορΜ3 κ xonoAHOMy pacTBopy, n nonyHeHHbin pacTBop npoMbiBatOT 15% BOAHbiM pacTBopoM HCI, -10- a nocne θτογο bohoū ao HeiiTpami3ai4W/i. ΧποροφορΜΟΒωίί cnofi cymaT, n pacTBopuTenb οτγόηηιοτ. Οοτβτοκ 3Τ3ηοπομ m cyuiaT.HaiiAeHo: 403,150 npnMep 9-unKnonponnn-6 ^ Top-7- / 4-Kap6O3TOKCn-1-Neptune3HHnn / -4-oKCO-1, 4-AnrnApoxnHonnH-3-Kap6oHOBa KncnoTa Ι-ΜΜΚΠΟΠρθΠΙ / 1Π-6-φΤθρ-7 -ΧΠθρ-4-ΟΚΟΟ-Ι, 4-ΑΜΠ / 1ΑρθΧΜΗΟΠΜΗ-3-Kap6oHOBy »o Kncnoiy (0.281 r, 0.001 μοππ) n l-Kap603T0Kcn Holiday3nH (0.632 r, 0.004 Mona) cycneHAnpyraT b 2-MeTnn-5-3TnnnnpnAHHe (8 μπ) n 1-MeTnn-nnpponnAOHe (2 μπ) n Biases b Tenei-ine 4 sacoB npn TeMnepaiype κηπβΗηη c očpaTHbiM xonoAnnbHnKOM headKunoHHon cMecn. Ilocne 3aBepiueHna headKLjnn Ao6aBnaK) T 20 μπ χποροφορΜ3 κ xonoAHOMy pacTBopy, n nonyHeHHbin pacTBop npoMbiBatOT 15% BOAHBM pacTBopo HCl, -10- a nocne θτογο boho ao HeiiTpami3ai4W / i. ΧποροφορΜΟΒωίί cnofi cymaT, n pacTBopuTenb οτγόηηιοτ. Οοτβτοκ 3Τ3ηοπομ m cyuiaT.
TaKMM o6pa30M nonyHaK)T l-i4HKnonponnn-6-0Top-7-/4-Kap6o3TOKcn/4-OKCO-l,4-AMrnApoxMHonMH-3-Kap6oHOByro KncnoTy (0,222 r, 55%) t. nnaBneHMfl 6onee 250°C. nonyHeHHbiM 4 npoflyKT nepeKpncTanni/i30BbiBaK>T M3 Ν,Ν—ΑΜΜΘΤΜΠφθρΜΒΜ11Α3. -11 - LV 10774TaKMM6pa30M nonyHaK) T1-4HKnonponnn-6-Top-7- / 4-Cape6TOKcn / 4-OKCO-1,4-AMrnApoxMHonMH-3-Kap6HOByro KncnoTy (0.222r, 55%) t. nnaBneHMfl 6onee 250 ° C. nonyHeHHbiM 4 npoflyKT nepeKpncTanni / i30BbiBaK > T M3 Ν, Ν — ΑΜΜΘΤΜΠφθρΜΒΜ11Α3. -11 to LV 10774
ΦΟΡΜΥΠΑ M30EPETEHM5RΦΟΡΜΥΠΑ M30EPETEHM5R
1. Cnocoč ποπγπθΗΜΛ l-3aMemeHHoPi 6^Top-4-oKco-7-/1-nnnepa3KHnn/-l,4-flMrMAp0XHH0nHH-3-Kap60H0B0ii KUCnOTbl φορΜγΠΝ I1. Cnocoč ποπγπθΗΜΛ 1-3aMemeHHoPi 6 ^ Top-4-oCco-7- / 1-naphtha3KHnn / -1, 4-flMrMAp0XHH0nHH-3-Kap60H0B0ii KUCnOTbl φορΜγΠΝ I
ΓΑΘ R - 3THn, ΜΜΚΠΟΠρΟΠΜΠ Ι/ΙΠΜ Π/1ΑΡΟΚΟΜ3ΤΜΠ, ΟΤΠΜΗΘΙΟΙΑΜίίΟΑ ΤΘΜ, HTO l-3aMemeHHyK> 6^Top-4-OKCo-7-/4-Kap6o3TOKcn-l-nnnepa3HHnn/-l,4- AnrnflpoxMHonMH-3-Kap6oHOByKD ΚΜΟποτγ μπμ ee cno>KHbiii 3φκρ ο6ιαθμ φορΜγπω II:ΓΑΘ R - 3THn, ΜΜΚΠΟΠρΟΠΜΠ Ι / ΙΠΜ Π / 1ΑΡΟΚΟΜ3ΤΜΠ, ΟΤΠΜΗΘΙΟΙΑΜίίΟΑ ΤΘΜ, HTO l-3aMemeHHyK > 6 ^ Top-4-OKCo-7- / 4-Capo-3TOKcn-1-Neptica3HHnn / -1, 4-AnrnflpoxMHonMH-3-Kap6oHOBYKD ΚΜΟποτγ μπμ ee cno; KHbiii 3φκρ ο6ιαθμ φορΜγπω II:
rfle R μμθθτ x<e 3Η3ηθηι/ια, hto y«a3aHbi Bbiiue, a R1 ηβπαθτοη boaopoaom nnn 3TUriOM,rfle r μμθθτ x < e 3Η3ηθηι / ια, hto y «a3aHbi Bbiiue, R1 ηβπαθτοη boaopoaom nnn 3TUriOM,
O noABepraiOT B03AeiicTBMfo menoHHoi/i cpeAbi. 2. Cnoco6 no nyHicry I, oinunaromnuicfl τθμ, hto b KanecTBe menoHHoii cpeAbi ncnonb3yioT cMecb aTaHona n βοαηογο pacTBopa ocHOBaHHa, τθκογο KaK KOH. 3. Cnoco6 no n. 1 h 2, omMHaKDLUniicfl τθμ, hto peatcunto βθαυγ npn TeMnepaType κιλπθημα peaKUnOHHoti CMecn. LV 10774 ΡΕΦΕΡΑΤO noABepraiOT B03AeiicTBMfo MenoHHi / i cpeAbi. 2. Cnoco6 no nyHicry I, oinunaromnuicfl τθμ, hto b KanecTBe menoHHoii cpeAbi ncnonb3yioT cMecb aTaHona n βοαηογο pacTBopa ocHOBaHHa, τθκογο KaK KOH. 3. Cnoco6 no n. 1 h 2, omMHaKDLUniicfl τθμ, hto main feed βθαυγ npn TeMnepaType κιλπθημα headKUnOHHoti CMecn. LV 10774 ΡΕΦΕΡΑΤ
CnOCo6 ΠΟΠγΗΘΗΙ/lfl 1 -33ΜΘ111ΘΗΗ0Μ 6-φΤθρ-4-ΟΚΟΟ-7-/1-ΠΜΠθρ33ΜΗΜΠ/-1,4-flHrHflp0XHH0nHH-3-Kap60H0B0M Kl/ICnOTblCnOCo6 ΠΟΠγΗΘΗΙ / lfl 1 -33ΜΘ111ΘΗΗ0Μ 6-φΤθρ-4-ΟΚΟΟ-7- / 1-ΠΜΠθρ33ΜΗΜΠ / -1,4-flHrHfp0XHH0nHH-3-Kap60H0B0M Kl / ICnOTbl
ΠρθβΠΟ>ΚΘΗ CI10C06 ΠΟΠγΗΘΗΜΑ 1-33ΜΘΙΜΘΗΗΟΜ-6-φΤθρ-4-ΟΚΟΟ-7-/1-ni/inepa3MHnn/-1^-AwrMflpoxiiHonviH-3-Kap6oHOBoii KucnoTbi očmeCi φopMyπbι I ο10ρθβΠΟ > ΚΘΗ CI10C06 ΠΟΠγΗΘΗΜΑ 1-33ΜΘΙΜΘΗΗΟΜ-6-φΤθρ-4-ΟΚΟΟ-7- / 1-ni / inepa3MHnn / -1 ^ -AwrMflpoxylHonviH-3-Kap6O-HOBoii
rfle R = CH2CH3, 141/ικηοπροπνιπ, CH2CH2OH, CH2OCH2CH2OH u b κοτοροΜ 1-3aMemeHHyio 6-φτορ-4-οκοο-7-/4-κ3ρ6θ3τοκαι-1-nnnepa3MHnn/-1,4-flnrMflpoxMHonMH-3-Kap6oHOByK} κΜοποτγ μπμ ee cnox<Hbiii 3TI/inOBblii 3φΜρ o6meii φορΜγπΝ II Οrfle R = CH2CH3, 141 / ικηοπροπνιπ, CH2CH2OH, CH2OCH2CH2OH ub κοτοροΜ 1-3aMemeHHyio 6-φτορ-4-οκοο-7- / 4-κ3ρ6θ3τοκαι-1-nept3 cnox < Hbiii 3TI / inOBblii 3φΜρ o6meii φορΜγπΝ II Ο
COOCH2CH3 rne R HMeeT yKa3aHHbie paHee 3HaH©Hmi, a R1 ββπηθτοα BonopoAOM μπμ θτμπομ, rnflponM3yioT b menoHHoii cpefle no ποπυηθημη οοθακηθημα I. ΠρθΑΠθ>κθΗ TaK>Ke cocTae ηοβογο οπο>κηογο 3<$\λρά φορΜγπΜ II μ cnocoč ero ποπυηθημβ.COOCH2CH3 RNE R HMeeT yKa3aHHbie paHee 3HaH © HMI to a R 1 ββπηθτοα BonopoAOM μπμ θτμπομ, rnflponM3yioT b menoHHoii cpefle of ποπυηθημη οοθακηθημα I. ΠρθΑΠθ > κθΗ Tak > Ke cocTae ηοβογο οπο > κηογο 3 < $ \ λρά φορΜγπΜ II μ cnocoč ero ποπυηθημβ.
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YU244787A YU46099B (en) | 1987-12-31 | 1987-12-31 | PROCESS FOR PREPARING 1-SUBSTITUTED 6-FLUORO-4-OXO-7- 1-PIPERAZINYL) -1 |
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LV10774A LV10774A (en) | 1995-08-20 |
LV10774B true LV10774B (en) | 1996-08-20 |
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AT (1) | AT396105B (en) |
CS (1) | CS274635B2 (en) |
DD (1) | DD283386B5 (en) |
HU (1) | HU200454B (en) |
LT (1) | LT3274B (en) |
LV (1) | LV10774B (en) |
NO (1) | NO885666L (en) |
PL (1) | PL163337B1 (en) |
PT (1) | PT89359B (en) |
RU (1) | RU2002744C1 (en) |
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US4017622A (en) * | 1972-12-18 | 1977-04-12 | Dainippon Pharmaceutical Co., Ltd. | Piperazine derivatives |
SE444566B (en) | 1977-09-20 | 1986-04-21 | Bellon Labor Sa Roger | 7-DIALKYLAMINE-6-HALOGEN-4-OXO-1,4-DIHYDROQINOLINE-3-CARBOXYLIC ACID, PROCEDURES FOR PREPARING THEREOF AND PHARMACEUTICAL PREPARATION OF THEREOF |
JPS5845426B2 (en) * | 1978-09-29 | 1983-10-08 | 杏林製薬株式会社 | Substituted quinoline carboxylic acid derivatives |
JPS5762259A (en) | 1980-09-05 | 1982-04-15 | Kyorin Pharmaceut Co Ltd | Preparation of substituted quinolinecarboxylic acid derivative |
DE3306771A1 (en) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | CHINOLONIC CARBONIC ACIDS, METHOD FOR THE PRODUCTION THEREOF AND THE ANTIBACTERIAL AGENTS CONTAINING THEM |
DE3308909A1 (en) | 1983-03-12 | 1984-09-13 | Bayer Ag, 5090 Leverkusen | BACTERICIDALS BASED ON CHINOLONIC CARBONIC ACID |
DE3509546A1 (en) * | 1985-03-16 | 1986-09-25 | Bayer Ag, 5090 Leverkusen | 7-AMINO-1- (SUBST.CYCLOPROPYL) -1,4-DIHYDRO-4-OXO-3-CHINOLINE CARBONIC ACIDS, METHOD FOR THE PRODUCTION THEREOF AND THE ANTIBACTERIAL AGENTS CONTAINING THEM |
JPH06103891B2 (en) | 1989-05-31 | 1994-12-14 | 日本電信電話株式会社 | Routing method for packet switching network |
JPH066686A (en) | 1992-06-17 | 1994-01-14 | Ricoh Co Ltd | Image pickup device |
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1987
- 1987-12-31 SI SI8712447A patent/SI8712447A8/en unknown
- 1987-12-31 YU YU244787A patent/YU46099B/en unknown
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1988
- 1988-12-21 NO NO88885666A patent/NO885666L/en unknown
- 1988-12-28 PT PT8935988A patent/PT89359B/en not_active IP Right Cessation
- 1988-12-29 CS CS903288A patent/CS274635B2/en unknown
- 1988-12-30 RU SU4613227 patent/RU2002744C1/en active
- 1988-12-30 AT AT320688A patent/AT396105B/en not_active IP Right Cessation
- 1988-12-30 PL PL27689088A patent/PL163337B1/en unknown
- 1988-12-30 DD DD32470388A patent/DD283386B5/en active IP Right Maintenance
- 1988-12-30 HU HU667788A patent/HU200454B/en not_active IP Right Cessation
-
1993
- 1993-05-05 LT LTIP510A patent/LT3274B/en not_active IP Right Cessation
- 1993-06-30 LV LV930828A patent/LV10774B/en unknown
Also Published As
Publication number | Publication date |
---|---|
HU200454B (en) | 1990-06-28 |
CS274635B2 (en) | 1991-09-15 |
LT3274B (en) | 1995-05-25 |
YU244787A (en) | 1990-06-30 |
PT89359B (en) | 1993-08-31 |
HUT49129A (en) | 1989-08-28 |
DD283386B5 (en) | 1997-10-30 |
ATA320688A (en) | 1992-10-15 |
PT89359A (en) | 1989-12-29 |
NO885666L (en) | 1989-07-03 |
YU46099B (en) | 1992-12-21 |
AT396105B (en) | 1993-06-25 |
RU2002744C1 (en) | 1993-11-15 |
PL163337B1 (en) | 1994-03-31 |
LTIP510A (en) | 1994-11-25 |
SI8712447A8 (en) | 1995-12-31 |
CS903288A2 (en) | 1990-12-13 |
NO885666D0 (en) | 1988-12-21 |
PL276890A1 (en) | 1989-10-16 |
LV10774A (en) | 1995-08-20 |
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