ES2861578T3 - Fluoración de sistemas de anillos aromáticos - Google Patents
Fluoración de sistemas de anillos aromáticos Download PDFInfo
- Publication number
- ES2861578T3 ES2861578T3 ES17173035T ES17173035T ES2861578T3 ES 2861578 T3 ES2861578 T3 ES 2861578T3 ES 17173035 T ES17173035 T ES 17173035T ES 17173035 T ES17173035 T ES 17173035T ES 2861578 T3 ES2861578 T3 ES 2861578T3
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- protecting group
- compound
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- aryl
- independently
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- 125000003118 aryl group Chemical group 0.000 title claims abstract description 49
- 238000004334 fluoridation Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 96
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 79
- 238000000034 method Methods 0.000 claims abstract description 78
- 238000010438 heat treatment Methods 0.000 claims abstract description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000000203 mixture Substances 0.000 claims abstract description 33
- 239000012454 non-polar solvent Substances 0.000 claims abstract description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 25
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims abstract description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims abstract description 10
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims abstract description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims abstract description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 7
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229940078552 o-xylene Drugs 0.000 claims abstract description 5
- -1 pxylene Chemical compound 0.000 claims description 64
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 15
- 125000006241 alcohol protecting group Chemical group 0.000 claims description 15
- 125000006244 carboxylic acid protecting group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical class C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 3
- 150000002159 estradiols Chemical class 0.000 claims description 3
- 150000002410 histidine derivatives Chemical class 0.000 claims description 3
- 150000002993 phenylalanine derivatives Chemical class 0.000 claims description 3
- 230000002285 radioactive effect Effects 0.000 claims description 3
- 150000003667 tyrosine derivatives Chemical class 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 97
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 41
- 238000002360 preparation method Methods 0.000 description 39
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 28
- 239000002904 solvent Substances 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 19
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 125000005520 diaryliodonium group Chemical group 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 239000002243 precursor Substances 0.000 description 15
- MOVBJUGHBJJKOW-UHFFFAOYSA-N methyl 2-amino-5-methoxybenzoate Chemical compound COC(=O)C1=CC(OC)=CC=C1N MOVBJUGHBJJKOW-UHFFFAOYSA-N 0.000 description 14
- 125000006239 protecting group Chemical group 0.000 description 13
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 0 *C(c1c(CC(C(O*)=O)N(*)c2ccccc2)cc(*)c(*)c1)I[Al] Chemical compound *C(c1c(CC(C(O*)=O)N(*)c2ccccc2)cc(*)c(*)c1)I[Al] 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000012955 diaryliodonium Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 239000002798 polar solvent Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- PAXWQORCRCBOCU-LURJTMIESA-N 6-fluoro-L-dopa Chemical compound OC(=O)[C@@H](N)CC1=CC(O)=C(O)C=C1F PAXWQORCRCBOCU-LURJTMIESA-N 0.000 description 7
- PNKCBKFRLOGSTG-UHFFFAOYSA-N CC(O)=O.CC(O)=O.COC(C=C1)=CC=C1I.COC(C=C1)=CC=C1I Chemical compound CC(O)=O.CC(O)=O.COC(C=C1)=CC=C1I.COC(C=C1)=CC=C1I PNKCBKFRLOGSTG-UHFFFAOYSA-N 0.000 description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 150000001501 aryl fluorides Chemical class 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- 239000011550 stock solution Substances 0.000 description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 125000005418 aryl aryl group Chemical group 0.000 description 6
- JCZSQOVZJXDMTK-UHFFFAOYSA-N iodo trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OI JCZSQOVZJXDMTK-UHFFFAOYSA-N 0.000 description 6
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 6
- CCSCCVLBMDKDBP-UHFFFAOYSA-N tributyl-(3,4-dimethoxyphenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(OC)C(OC)=C1 CCSCCVLBMDKDBP-UHFFFAOYSA-N 0.000 description 6
- WGAFQMMKTNUYDH-UHFFFAOYSA-N 2-(2-bromo-4,5-dimethoxyphenyl)ethanamine Chemical compound COC1=CC(Br)=C(CCN)C=C1OC WGAFQMMKTNUYDH-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 5
- 239000004810 polytetrafluoroethylene Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- GRUPMMBRLDBTDD-UHFFFAOYSA-N 3-[2-(2-methyl-1,3-thiazol-4-yl)ethynyl]benzonitrile Chemical compound S1C(C)=NC(C#CC=2C=C(C=CC=2)C#N)=C1 GRUPMMBRLDBTDD-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- 238000002600 positron emission tomography Methods 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- AUFVJZSDSXXFOI-UHFFFAOYSA-N 2.2.2-cryptand Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCCOCC2 AUFVJZSDSXXFOI-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- STWXDDJLAMTLIB-UHFFFAOYSA-M bis(4-methoxyphenyl)iodanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=CC(OC)=CC=C1[I+]C1=CC=C(OC)C=C1 STWXDDJLAMTLIB-UHFFFAOYSA-M 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- KRHYYFGTRYWZRS-BJUDXGSMSA-M fluorine-18(1-) Chemical compound [18F-] KRHYYFGTRYWZRS-BJUDXGSMSA-M 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- VVOKQULHZGRCQE-UHFFFAOYSA-N 2-[2-(2-bromo-4,5-dimethoxyphenyl)ethyl]isoindole-1,3-dione Chemical compound C1=C(OC)C(OC)=CC(Br)=C1CCN1C(=O)C2=CC=CC=C2C1=O VVOKQULHZGRCQE-UHFFFAOYSA-N 0.000 description 2
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical group NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
- 229910019398 NaPF6 Inorganic materials 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- DSALILVWXNPMMK-UHFFFAOYSA-M bis(4-methoxyphenyl)iodanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC(OC)=CC=C1[I+]C1=CC=C(OC)C=C1 DSALILVWXNPMMK-UHFFFAOYSA-M 0.000 description 2
- KVGPQVFGSFMCTA-UHFFFAOYSA-M bis(4-methoxyphenyl)iodanium;fluoride Chemical compound [F-].C1=CC(OC)=CC=C1[I+]C1=CC=C(OC)C=C1 KVGPQVFGSFMCTA-UHFFFAOYSA-M 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 150000003983 crown ethers Chemical class 0.000 description 2
- 239000002739 cryptand Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000001722 flash pyrolysis Methods 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 150000002222 fluorine compounds Chemical group 0.000 description 2
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 2
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- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011426 transformation method Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
- C07C271/66—Y being a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10715608P | 2008-10-21 | 2008-10-21 | |
| US23603709P | 2009-08-21 | 2009-08-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2861578T3 true ES2861578T3 (es) | 2021-10-06 |
Family
ID=42119938
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES17173035T Active ES2861578T3 (es) | 2008-10-21 | 2009-10-20 | Fluoración de sistemas de anillos aromáticos |
| ES12185395.6T Active ES2627825T3 (es) | 2008-10-21 | 2009-10-20 | Fluoración de sistemas de anillos aromáticos |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12185395.6T Active ES2627825T3 (es) | 2008-10-21 | 2009-10-20 | Fluoración de sistemas de anillos aromáticos |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8604213B2 (enExample) |
| EP (3) | EP2349977A4 (enExample) |
| JP (2) | JP2012506440A (enExample) |
| AU (1) | AU2009307715B2 (enExample) |
| CA (1) | CA2741967A1 (enExample) |
| ES (2) | ES2861578T3 (enExample) |
| WO (1) | WO2010048170A2 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2861578T3 (es) | 2008-10-21 | 2021-10-06 | Nutech Ventures | Fluoración de sistemas de anillos aromáticos |
| US9302990B2 (en) * | 2008-10-21 | 2016-04-05 | Nutech Ventures | Fluorination of aromatic ring systems |
| US8377704B2 (en) * | 2009-10-20 | 2013-02-19 | Nutech Ventures | Detection and quantification of anions |
| US8546578B2 (en) * | 2010-02-04 | 2013-10-01 | Nutech Ventures | Iodonium Cyclophanes for SECURE arene functionalization |
| US20120309796A1 (en) | 2011-06-06 | 2012-12-06 | Fariborz Firooznia | Benzocycloheptene acetic acids |
| CA2875622A1 (en) | 2012-06-05 | 2013-12-12 | Nutech Ventures | Processes and reagents for making diaryliodonium salts |
| WO2014022224A1 (en) * | 2012-08-02 | 2014-02-06 | The Penn State Research Foundation | Polymer conductor for lithium-ion batteries |
| WO2014052650A2 (en) * | 2012-09-26 | 2014-04-03 | Massachusetts Institute Of Technology | Modification of peptides via snar reactions of thiols with fluorinated aromatics |
| JP2016503401A (ja) * | 2012-10-27 | 2016-02-04 | グランド・フルーア・ファーマスーティカルズ・インコーポレイテッド | ジアリールヨードニウム塩を製造するための方法及び試薬 |
| WO2015147950A2 (en) * | 2014-01-03 | 2015-10-01 | Nutech Ventures | Radioiodinated compounds |
| US10071943B2 (en) | 2014-04-11 | 2018-09-11 | The Regents Of The University Of Michigan | Copper catalyzed [18F]fluorination of iodonium salts |
| US9181297B1 (en) | 2014-05-15 | 2015-11-10 | Massachusetts Institute Of Technology | Cysteine arylation directed by a genetically encodable π-clamp |
| US20170001957A1 (en) * | 2015-06-12 | 2017-01-05 | Nutech Ventures | Radioiodinated bioconjugation reagents |
| CN109384806B (zh) * | 2017-08-03 | 2021-04-27 | 王璐 | 一种[18f]fbpa新型制备方法 |
| JP7545813B2 (ja) * | 2019-04-24 | 2024-09-05 | 住友化学株式会社 | レジスト組成物及びレジストパターンの製造方法 |
| CN110862367A (zh) * | 2019-11-18 | 2020-03-06 | 上海兆维科技发展有限公司 | 一种香豆素芳基醚类化合物及其制备方法与应用 |
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| JPH0611718B2 (ja) * | 1986-06-26 | 1994-02-16 | 財団法人相模中央化学研究所 | 芳香族フツ素化合物の製造方法 |
| GB0115927D0 (en) | 2001-06-29 | 2001-08-22 | Nycomed Amersham Plc | Solid-phase nucleophilic fluorination |
| GB0206117D0 (en) | 2002-03-15 | 2002-04-24 | Imaging Res Solutions Ltd | Use of microfabricated devices |
| GB0229683D0 (en) | 2002-12-20 | 2003-01-29 | Imaging Res Solutions Ltd | Preparation of radiopharmaceuticals |
| GB0320313D0 (en) | 2003-08-29 | 2003-10-01 | Ic Innovations Ltd | Process |
| GB0329716D0 (en) * | 2003-12-23 | 2004-01-28 | Amersham Plc | Radical trap |
| GB0407952D0 (en) | 2004-04-08 | 2004-05-12 | Amersham Plc | Fluoridation method |
| US20060128031A1 (en) | 2004-12-15 | 2006-06-15 | Robotti Karla M | Addressable recovery of bound analytes from an evanescent wave sensor |
| JP4931181B2 (ja) * | 2006-01-31 | 2012-05-16 | 独立行政法人放射線医学総合研究所 | １８ｆ標識フルオロベンゼン環を有する放射性リガンドの合成法 |
| PT2046396E (pt) | 2006-07-18 | 2013-12-09 | Univ Nebraska | Agentes de fluoração anidro 18f radioactivamente marcados e métodos para a sua produção e utilização |
| GB0808986D0 (en) | 2008-05-16 | 2008-06-25 | Univ Newcastle | Formation of 18F and 19F fluoroarenes bearing reactive functionalities |
| EP2307337B1 (en) | 2008-07-14 | 2016-01-13 | The Regents of The University of California | Nucleophilic fluorination of aromatic compounds |
| GB0814893D0 (en) | 2008-08-14 | 2008-09-17 | Ge Healthcare Ltd | Improved fluoridation of iodonium salts |
| US9302990B2 (en) | 2008-10-21 | 2016-04-05 | Nutech Ventures | Fluorination of aromatic ring systems |
| ES2861578T3 (es) | 2008-10-21 | 2021-10-06 | Nutech Ventures | Fluoración de sistemas de anillos aromáticos |
| US8377704B2 (en) | 2009-10-20 | 2013-02-19 | Nutech Ventures | Detection and quantification of anions |
| US8546578B2 (en) | 2010-02-04 | 2013-10-01 | Nutech Ventures | Iodonium Cyclophanes for SECURE arene functionalization |
-
2009
- 2009-10-20 ES ES17173035T patent/ES2861578T3/es active Active
- 2009-10-20 EP EP09822555A patent/EP2349977A4/en not_active Withdrawn
- 2009-10-20 US US13/125,209 patent/US8604213B2/en active Active
- 2009-10-20 ES ES12185395.6T patent/ES2627825T3/es active Active
- 2009-10-20 EP EP12185395.6A patent/EP2537826B1/en active Active
- 2009-10-20 AU AU2009307715A patent/AU2009307715B2/en active Active
- 2009-10-20 WO PCT/US2009/061308 patent/WO2010048170A2/en not_active Ceased
- 2009-10-20 EP EP17173035.1A patent/EP3284736B1/en active Active
- 2009-10-20 CA CA2741967A patent/CA2741967A1/en not_active Abandoned
- 2009-10-20 JP JP2011533270A patent/JP2012506440A/ja not_active Withdrawn
-
2015
- 2015-05-27 JP JP2015107073A patent/JP6049804B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP6049804B2 (ja) | 2016-12-21 |
| EP3284736A1 (en) | 2018-02-21 |
| EP3284736B1 (en) | 2021-03-03 |
| US20120004417A1 (en) | 2012-01-05 |
| AU2009307715B2 (en) | 2015-08-27 |
| EP2537826B1 (en) | 2017-03-08 |
| WO2010048170A3 (en) | 2010-07-08 |
| AU2009307715A1 (en) | 2010-04-29 |
| EP2349977A2 (en) | 2011-08-03 |
| JP2012506440A (ja) | 2012-03-15 |
| ES2627825T3 (es) | 2017-07-31 |
| JP2015180668A (ja) | 2015-10-15 |
| EP2349977A4 (en) | 2012-03-28 |
| CA2741967A1 (en) | 2010-04-29 |
| EP2537826A1 (en) | 2012-12-26 |
| US8604213B2 (en) | 2013-12-10 |
| WO2010048170A2 (en) | 2010-04-29 |
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