TWI577663B - 用於製備４－胺基－５－氟－３－鹵素－６－（經取代之）吡啶甲酸酯的方法 - Google Patents
用於製備４－胺基－５－氟－３－鹵素－６－（經取代之）吡啶甲酸酯的方法 Download PDFInfo
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- TWI577663B TWI577663B TW102126266A TW102126266A TWI577663B TW I577663 B TWI577663 B TW I577663B TW 102126266 A TW102126266 A TW 102126266A TW 102126266 A TW102126266 A TW 102126266A TW I577663 B TWI577663 B TW I577663B
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- alkyl
- halogen
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- 238000000034 method Methods 0.000 title claims description 72
- 238000002360 preparation method Methods 0.000 title description 28
- 230000008569 process Effects 0.000 title description 24
- 150000001875 compounds Chemical class 0.000 claims description 328
- 238000006243 chemical reaction Methods 0.000 claims description 146
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 85
- 239000000460 chlorine Substances 0.000 claims description 76
- 229910052736 halogen Inorganic materials 0.000 claims description 76
- -1 C 1 -C 4 alkyl Chemical group 0.000 claims description 72
- 229910052801 chlorine Inorganic materials 0.000 claims description 64
- 150000002367 halogens Chemical class 0.000 claims description 61
- 229910052794 bromium Inorganic materials 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 41
- 239000003054 catalyst Substances 0.000 claims description 39
- 229910052740 iodine Inorganic materials 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 35
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 34
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 26
- 238000005859 coupling reaction Methods 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 25
- 230000002140 halogenating effect Effects 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 24
- 239000012453 solvate Substances 0.000 claims description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- 229910052802 copper Inorganic materials 0.000 claims description 22
- 239000010949 copper Substances 0.000 claims description 22
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 21
- 229910052723 transition metal Inorganic materials 0.000 claims description 21
- 150000003624 transition metals Chemical class 0.000 claims description 21
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 18
- 125000003277 amino group Chemical group 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 230000008878 coupling Effects 0.000 claims description 16
- 238000010168 coupling process Methods 0.000 claims description 16
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- 229910021529 ammonia Inorganic materials 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 239000011698 potassium fluoride Substances 0.000 claims description 11
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 238000003682 fluorination reaction Methods 0.000 claims description 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 7
- 229910001515 alkali metal fluoride Inorganic materials 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 150000003983 crown ethers Chemical class 0.000 claims description 6
- 235000003270 potassium fluoride Nutrition 0.000 claims description 6
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 238000010511 deprotection reaction Methods 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 239000011775 sodium fluoride Substances 0.000 claims description 2
- 235000013024 sodium fluoride Nutrition 0.000 claims description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 2
- PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical group C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 claims 1
- 150000003990 18-crown-6 derivatives Chemical group 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical class CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- 239000000203 mixture Substances 0.000 description 50
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 47
- 239000011541 reaction mixture Substances 0.000 description 45
- 239000007787 solid Substances 0.000 description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- 150000004820 halides Chemical class 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- 238000004949 mass spectrometry Methods 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 15
- 125000005843 halogen group Chemical group 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 235000017168 chlorine Nutrition 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 125000001153 fluoro group Chemical group F* 0.000 description 12
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- 239000011737 fluorine Substances 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 239000012442 inert solvent Substances 0.000 description 9
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 7
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 7
- AIYYMMQIMJOTBM-UHFFFAOYSA-L nickel(ii) acetate Chemical compound [Ni+2].CC([O-])=O.CC([O-])=O AIYYMMQIMJOTBM-UHFFFAOYSA-L 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 6
- 150000002148 esters Chemical group 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- MUCAKBKIVUFYQH-UHFFFAOYSA-N propan-2-yl 4,5,6-trichloropyridine-2-carboxylate Chemical compound CC(C)OC(=O)C1=CC(Cl)=C(Cl)C(Cl)=N1 MUCAKBKIVUFYQH-UHFFFAOYSA-N 0.000 description 6
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- YRGNDQQIUXCCAI-UHFFFAOYSA-N propan-2-yl 4,5,6-trifluoropyridine-2-carboxylate Chemical compound CC(C)OC(=O)C1=CC(F)=C(F)C(F)=N1 YRGNDQQIUXCCAI-UHFFFAOYSA-N 0.000 description 5
- CICGUYUXQJWNFS-UHFFFAOYSA-N propan-2-yl 4-amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate Chemical compound COC1=C(Cl)C=CC(C=2C(=C(N)C=C(N=2)C(=O)OC(C)C)F)=C1F CICGUYUXQJWNFS-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- 238000005576 amination reaction Methods 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 4
- 239000012320 chlorinating reagent Substances 0.000 description 4
- 239000008139 complexing agent Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 238000012544 monitoring process Methods 0.000 description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- BRIULBRBZYPEDW-UHFFFAOYSA-N propan-2-yl 4-amino-6-bromo-5-fluoropyridine-2-carboxylate Chemical compound CC(C)OC(=O)C1=CC(N)=C(F)C(Br)=N1 BRIULBRBZYPEDW-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XDLNRRRJZOJTRW-UHFFFAOYSA-N thiohypochlorous acid Chemical compound ClS XDLNRRRJZOJTRW-UHFFFAOYSA-N 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
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- IGPQMIDJMOHHMP-UHFFFAOYSA-N 2,3,4-trichloropyridin-1-ium chloride Chemical compound [Cl-].ClC1=CC=[NH+]C(=C1Cl)Cl IGPQMIDJMOHHMP-UHFFFAOYSA-N 0.000 description 3
- 102100027324 2-hydroxyacyl-CoA lyase 1 Human genes 0.000 description 3
- PJAIMBYNTXNOCN-UHFFFAOYSA-N 3,6-dibromo-1h-indole Chemical compound BrC1=CC=C2C(Br)=CNC2=C1 PJAIMBYNTXNOCN-UHFFFAOYSA-N 0.000 description 3
- HBPSHBLIEQWDMD-UHFFFAOYSA-N 4,5-dichloro-6-phenylpyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=C(Cl)C(C=2C=CC=CC=2)=N1 HBPSHBLIEQWDMD-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 101001009252 Homo sapiens 2-hydroxyacyl-CoA lyase 1 Proteins 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- VEOLKVPRMPFSNF-UHFFFAOYSA-M [Cl-].Cl[N+]1=CC=CC=C1 Chemical compound [Cl-].Cl[N+]1=CC=CC=C1 VEOLKVPRMPFSNF-UHFFFAOYSA-M 0.000 description 3
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical group [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- KRZUZKOBHVZRON-UHFFFAOYSA-N propan-2-yl 4-amino-5,6-difluoropyridine-2-carboxylate Chemical compound CC(C)OC(=O)C1=CC(N)=C(F)C(F)=N1 KRZUZKOBHVZRON-UHFFFAOYSA-N 0.000 description 3
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- MWDNZMWVENFVHT-UHFFFAOYSA-L (2-decoxy-2-oxoethyl)-[2-[2-[(2-decoxy-2-oxoethyl)-dimethylazaniumyl]ethylsulfanyl]ethyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCOC(=O)C[N+](C)(C)CCSCC[N+](C)(C)CC(=O)OCCCCCCCCCC MWDNZMWVENFVHT-UHFFFAOYSA-L 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
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- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- LWABFMLTBBNLTA-UHFFFAOYSA-N cyclobutyl carbamate Chemical compound NC(=O)OC1CCC1 LWABFMLTBBNLTA-UHFFFAOYSA-N 0.000 description 1
- AUELWJRRASQDKI-UHFFFAOYSA-N cyclohexyl carbamate Chemical compound NC(=O)OC1CCCCC1 AUELWJRRASQDKI-UHFFFAOYSA-N 0.000 description 1
- WZOVRVYGPDTSSI-UHFFFAOYSA-N cyclopentyl n-aminocarbamate Chemical compound NNC(=O)OC1CCCC1 WZOVRVYGPDTSSI-UHFFFAOYSA-N 0.000 description 1
- VBJNVGFACHOKLX-UHFFFAOYSA-N cyclopropylmethyl N-aminocarbamate Chemical compound C1(CC1)COC(=O)NN VBJNVGFACHOKLX-UHFFFAOYSA-N 0.000 description 1
- VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ACYGYJFTZSAZKR-UHFFFAOYSA-J dicalcium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Ca+2].[Ca+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O ACYGYJFTZSAZKR-UHFFFAOYSA-J 0.000 description 1
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- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
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- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
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- CVYZJUXLXNJDEU-UHFFFAOYSA-N methyl 4-amino-6-bromo-3-chloro-5-fluoropyridine-2-carboxylate Chemical compound COC(=O)C1=NC(Br)=C(F)C(N)=C1Cl CVYZJUXLXNJDEU-UHFFFAOYSA-N 0.000 description 1
- GJRCHXIGVQXIPY-UHFFFAOYSA-N methyl 4-amino-6-bromo-5-fluoropyridine-2-carboxylate Chemical compound COC(=O)C1=CC(N)=C(F)C(Br)=N1 GJRCHXIGVQXIPY-UHFFFAOYSA-N 0.000 description 1
- ODRFMIJNQNBMMJ-UHFFFAOYSA-N methyl 6-(4-chloro-2-fluoro-3-methoxyphenyl)-4,5-difluoropyridine-2-carboxylate Chemical compound COC(=O)C1=CC(F)=C(F)C(C=2C(=C(OC)C(Cl)=CC=2)F)=N1 ODRFMIJNQNBMMJ-UHFFFAOYSA-N 0.000 description 1
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- 239000003880 polar aprotic solvent Substances 0.000 description 1
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- CUCADYTVGOVTKY-UHFFFAOYSA-N propan-2-yl 4,5-difluoro-6-(4-methoxyphenyl)pyridine-2-carboxylate Chemical compound C1=CC(OC)=CC=C1C1=NC(C(=O)OC(C)C)=CC(F)=C1F CUCADYTVGOVTKY-UHFFFAOYSA-N 0.000 description 1
- PCHKPGRAPBRHIZ-UHFFFAOYSA-N propan-2-yl 4,5-difluoro-6-phenylpyridine-2-carboxylate Chemical compound CC(C)OC(=O)C1=CC(F)=C(F)C(C=2C=CC=CC=2)=N1 PCHKPGRAPBRHIZ-UHFFFAOYSA-N 0.000 description 1
- FHCDQJCSRTZQJW-UHFFFAOYSA-N propan-2-yl 4-acetamido-6-chloro-5-fluoropyridine-2-carboxylate Chemical compound CC(C)OC(=O)C1=CC(NC(C)=O)=C(F)C(Cl)=N1 FHCDQJCSRTZQJW-UHFFFAOYSA-N 0.000 description 1
- PIBVWUSLWKKFOU-UHFFFAOYSA-N propan-2-yl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate Chemical compound COC1=C(Cl)C=CC(C=2C(=C(N)C(Cl)=C(C(=O)OC(C)C)N=2)F)=C1F PIBVWUSLWKKFOU-UHFFFAOYSA-N 0.000 description 1
- FWPXDYCSECBKSZ-UHFFFAOYSA-N propan-2-yl 6-(4-chlorophenyl)-4,5-difluoropyridine-2-carboxylate Chemical compound CC(C)OC(=O)C1=CC(F)=C(F)C(C=2C=CC(Cl)=CC=2)=N1 FWPXDYCSECBKSZ-UHFFFAOYSA-N 0.000 description 1
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- 230000005588 protonation Effects 0.000 description 1
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- 230000009467 reduction Effects 0.000 description 1
- BDEZGPKAMAVGBE-UHFFFAOYSA-N s-(3-nitropyridin-2-yl)thiohydroxylamine Chemical compound NSC1=NC=CC=C1[N+]([O-])=O BDEZGPKAMAVGBE-UHFFFAOYSA-N 0.000 description 1
- LOFZYSZWOLKUGE-UHFFFAOYSA-N s-benzyl carbamothioate Chemical compound NC(=O)SCC1=CC=CC=C1 LOFZYSZWOLKUGE-UHFFFAOYSA-N 0.000 description 1
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- UGJCNRLBGKEGEH-UHFFFAOYSA-N sodium-binding benzofuran isophthalate Chemical compound COC1=CC=2C=C(C=3C(=CC(=CC=3)C(O)=O)C(O)=O)OC=2C=C1N(CCOCC1)CCOCCOCCN1C(C(=CC=1C=2)OC)=CC=1OC=2C1=CC=C(C(O)=O)C=C1C(O)=O UGJCNRLBGKEGEH-UHFFFAOYSA-N 0.000 description 1
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- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
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- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 150000003544 thiamines Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical group SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- PIZNQHDTOZMVBH-UHFFFAOYSA-N thionylimide Chemical compound N=S=O PIZNQHDTOZMVBH-UHFFFAOYSA-N 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 150000004684 trihydrates Chemical class 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
- BPIBEKPIZVPARD-UHFFFAOYSA-N triphenylmethanesulfinamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(S(=O)N)C1=CC=CC=C1 BPIBEKPIZVPARD-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005303 weighing Methods 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
- C07D213/60—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 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261675235P | 2012-07-24 | 2012-07-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201406726A TW201406726A (zh) | 2014-02-16 |
| TWI577663B true TWI577663B (zh) | 2017-04-11 |
Family
ID=48901197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW102126266A TWI577663B (zh) | 2012-07-24 | 2013-07-23 | 用於製備４－胺基－５－氟－３－鹵素－６－（經取代之）吡啶甲酸酯的方法 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US8871943B2 (enExample) |
| EP (1) | EP2877453B1 (enExample) |
| JP (1) | JP6046817B2 (enExample) |
| KR (1) | KR101946681B1 (enExample) |
| CN (1) | CN104640844B (enExample) |
| AR (1) | AR091856A1 (enExample) |
| AU (1) | AU2013293200B2 (enExample) |
| BR (1) | BR112015001615B8 (enExample) |
| CA (1) | CA2879530C (enExample) |
| CO (1) | CO7200265A2 (enExample) |
| IL (1) | IL236816A (enExample) |
| IN (1) | IN2015DN00821A (enExample) |
| MX (1) | MX351886B (enExample) |
| NZ (1) | NZ704103A (enExample) |
| PL (1) | PL2877453T3 (enExample) |
| RU (1) | RU2632203C2 (enExample) |
| TW (1) | TWI577663B (enExample) |
| UY (1) | UY34946A (enExample) |
| WO (1) | WO2014018502A1 (enExample) |
| ZA (1) | ZA201500701B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR092355A1 (es) * | 2012-07-24 | 2015-04-15 | Dow Agrosciences Llc | Fluoruros de fluoropicolinoilo y procesos para su preparacion |
| US8764316B1 (en) | 2013-05-23 | 2014-07-01 | Corning Cable Systems Llc | Fiber optic connector with vented ferrule holder |
| TW201609651A (zh) | 2013-11-12 | 2016-03-16 | 陶氏農業科學公司 | 用於氟化化合物之過程（一） |
| BR102014028164A2 (pt) * | 2013-11-12 | 2015-09-08 | Dow Agrosciences Llc | processo para fluoração de compostos |
| TW201609652A (zh) | 2013-11-12 | 2016-03-16 | 陶氏農業科學公司 | 用於氟化化合物之過程（三） |
| TWI726900B (zh) | 2015-08-04 | 2021-05-11 | 美商陶氏農業科學公司 | 用於氟化化合物之過程 |
| CA3012167A1 (en) * | 2016-01-22 | 2017-07-27 | Dow Agrosciences Llc | Process for the preparation of 4-alkoxy-3-acetoxypicolinic acids |
| BR112018073348B8 (pt) * | 2016-05-19 | 2023-05-16 | Dow Agrosciences Llc | Métodos para preparar 6-aril-4-aminopicolinatos e 2-aril-6-aminopirimidina-4-carboxilatos por acoplamento direto de suzuki |
| EP3555049A4 (en) * | 2016-12-13 | 2020-04-29 | Dow AgroSciences LLC | Method of preparing benzy 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinate |
| EP3853205A1 (en) * | 2018-09-19 | 2021-07-28 | Corteva Agriscience LLC | Preparation of halogen analogs of picloram |
| BR112022018508A2 (pt) * | 2020-03-18 | 2022-10-25 | Corteva Agriscience Llc | Síntese melhorada de 4-amino-6-(heterocíclico)picolinatos |
| CN114702440B (zh) * | 2022-04-26 | 2024-06-18 | 永农生物科学有限公司 | 一种氨氯吡啶酸的制备方法及制备的氨氯吡啶酸 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003101926A1 (de) * | 2002-06-04 | 2003-12-11 | Clariant Gmbh | Verfahren zur herstellung von fluor enthaltenden verbindungen über fluor-halogenaustausch durch spezielle polyaminophosphazen-katalysatoren |
| TW200512194A (en) * | 2003-04-02 | 2005-04-01 | Dow Agrosciences Llc | 6-alkyl or alkenyl-4-aminopicolinates and their use as herbicides |
| TW200736224A (en) * | 2006-01-13 | 2007-10-01 | Dow Agrosciences Llc | 6-(Poly-substituted aryl)-4-aminopicolinates and their use as herbicides |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2520254B2 (ja) * | 1987-04-28 | 1996-07-31 | イハラケミカル工業株式会社 | ３，４，５−トリフルオロ安息香酸誘導体およびその製造方法 |
| US4847442A (en) * | 1988-07-18 | 1989-07-11 | Allied-Signal Inc. | Process for the preparation of difluorobenzenes |
| US6297197B1 (en) | 2000-01-14 | 2001-10-02 | Dow Agrosciences Llc | 4-aminopicolinates and their use as herbicides |
| AR037228A1 (es) | 2001-07-30 | 2004-11-03 | Dow Agrosciences Llc | Compuestos del acido 6-(aril o heteroaril)-4-aminopicolinico, composicion herbicida que los comprende y metodo para controlar vegetacion no deseada |
| TWI529163B (zh) | 2011-01-25 | 2016-04-11 | 陶氏農業科學公司 | 用於製備４－胺基－５－氟－３－鹵素－６－（經取代之）吡啶甲酸酯的方法 |
| TWI537252B (zh) | 2011-01-25 | 2016-06-11 | 陶氏農業科學公司 | 用於製備４－胺基－５－氟－３－鹵素－６－（經取代之）吡啶甲酸酯的方法（一） |
-
2013
- 2013-07-22 AR ARP130102597A patent/AR091856A1/es active IP Right Grant
- 2013-07-23 EP EP13742581.5A patent/EP2877453B1/en active Active
- 2013-07-23 WO PCT/US2013/051623 patent/WO2014018502A1/en not_active Ceased
- 2013-07-23 RU RU2015106019A patent/RU2632203C2/ru active
- 2013-07-23 PL PL13742581T patent/PL2877453T3/pl unknown
- 2013-07-23 NZ NZ704103A patent/NZ704103A/en unknown
- 2013-07-23 CN CN201380048518.6A patent/CN104640844B/zh active Active
- 2013-07-23 CA CA2879530A patent/CA2879530C/en active Active
- 2013-07-23 TW TW102126266A patent/TWI577663B/zh active
- 2013-07-23 US US13/949,060 patent/US8871943B2/en active Active
- 2013-07-23 MX MX2015001141A patent/MX351886B/es active IP Right Grant
- 2013-07-23 BR BR112015001615A patent/BR112015001615B8/pt active IP Right Grant
- 2013-07-23 UY UY0001034946A patent/UY34946A/es active IP Right Grant
- 2013-07-23 KR KR1020157004099A patent/KR101946681B1/ko active Active
- 2013-07-23 AU AU2013293200A patent/AU2013293200B2/en active Active
- 2013-07-23 IN IN821DEN2015 patent/IN2015DN00821A/en unknown
- 2013-07-23 JP JP2015524380A patent/JP6046817B2/ja active Active
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2015
- 2015-01-20 IL IL236816A patent/IL236816A/en active IP Right Grant
- 2015-01-30 ZA ZA2015/00701A patent/ZA201500701B/en unknown
- 2015-02-06 CO CO15024012A patent/CO7200265A2/es unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003101926A1 (de) * | 2002-06-04 | 2003-12-11 | Clariant Gmbh | Verfahren zur herstellung von fluor enthaltenden verbindungen über fluor-halogenaustausch durch spezielle polyaminophosphazen-katalysatoren |
| TW200512194A (en) * | 2003-04-02 | 2005-04-01 | Dow Agrosciences Llc | 6-alkyl or alkenyl-4-aminopicolinates and their use as herbicides |
| TW200736224A (en) * | 2006-01-13 | 2007-10-01 | Dow Agrosciences Llc | 6-(Poly-substituted aryl)-4-aminopicolinates and their use as herbicides |
Also Published As
| Publication number | Publication date |
|---|---|
| AR091856A1 (es) | 2015-03-04 |
| BR112015001615B1 (pt) | 2019-10-22 |
| PL2877453T3 (pl) | 2017-08-31 |
| KR101946681B1 (ko) | 2019-02-11 |
| MX351886B (es) | 2017-11-01 |
| US20140031556A1 (en) | 2014-01-30 |
| EP2877453B1 (en) | 2016-07-06 |
| CO7200265A2 (es) | 2015-02-27 |
| CN104640844A (zh) | 2015-05-20 |
| CA2879530A1 (en) | 2014-01-30 |
| UY34946A (es) | 2014-02-28 |
| IL236816A (en) | 2016-11-30 |
| NZ704103A (en) | 2016-08-26 |
| BR112015001615A2 (pt) | 2017-07-04 |
| AU2013293200A1 (en) | 2015-02-19 |
| WO2014018502A1 (en) | 2014-01-30 |
| IN2015DN00821A (enExample) | 2015-06-12 |
| BR112015001615B8 (pt) | 2022-08-23 |
| EP2877453A1 (en) | 2015-06-03 |
| JP2015530367A (ja) | 2015-10-15 |
| US8871943B2 (en) | 2014-10-28 |
| JP6046817B2 (ja) | 2016-12-21 |
| RU2015106019A (ru) | 2016-09-10 |
| CA2879530C (en) | 2019-06-18 |
| CN104640844B (zh) | 2016-11-09 |
| HK1210613A1 (en) | 2016-04-29 |
| TW201406726A (zh) | 2014-02-16 |
| KR20150036673A (ko) | 2015-04-07 |
| RU2632203C2 (ru) | 2017-10-03 |
| MX2015001141A (es) | 2015-09-08 |
| AU2013293200B2 (en) | 2016-11-17 |
| ZA201500701B (en) | 2016-10-26 |
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