JP5611043B2 - 4−アミノブタ−2−エノリド類を調製する方法 - Google Patents
4−アミノブタ−2−エノリド類を調製する方法 Download PDFInfo
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- JP5611043B2 JP5611043B2 JP2010525229A JP2010525229A JP5611043B2 JP 5611043 B2 JP5611043 B2 JP 5611043B2 JP 2010525229 A JP2010525229 A JP 2010525229A JP 2010525229 A JP2010525229 A JP 2010525229A JP 5611043 B2 JP5611043 B2 JP 5611043B2
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- general formula
- compound
- alkyl
- haloalkyl
- arylalkyl
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- JWXMVJRAFLUMBC-UHFFFAOYSA-N 2-amino-2h-furan-5-one Chemical class NC1OC(=O)C=C1 JWXMVJRAFLUMBC-UHFFFAOYSA-N 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 title description 5
- -1 4-aminobut-2-enolide compound Chemical class 0.000 claims description 88
- 150000001875 compounds Chemical class 0.000 claims description 59
- 238000002360 preparation method Methods 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000001188 haloalkyl group Chemical group 0.000 claims description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 239000007858 starting material Substances 0.000 claims description 17
- 239000000460 chlorine Chemical group 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 239000011734 sodium Substances 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 3
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 3
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 150000001540 azides Chemical group 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 30
- 239000000203 mixture Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 9
- 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 8
- 150000001412 amines Chemical class 0.000 description 8
- PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical compound CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 7
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 7
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 229920002359 Tetronic® Polymers 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- QOIYTRGFOFZNKF-UHFFFAOYSA-N flupyradifurone Chemical compound C=1C(=O)OCC=1N(CC(F)F)CC1=CC=C(Cl)N=C1 QOIYTRGFOFZNKF-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000009666 routine test Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- XALCOJXGWJXWBL-UHFFFAOYSA-N 1-(6-chloropyridin-3-yl)-n-methylmethanamine Chemical compound CNCC1=CC=C(Cl)N=C1 XALCOJXGWJXWBL-UHFFFAOYSA-N 0.000 description 2
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 2
- ZNOVTXRBGFNYRX-UHFFFAOYSA-N 2-[[4-[(2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 ZNOVTXRBGFNYRX-UHFFFAOYSA-N 0.000 description 2
- XSJVWZAETSBXKU-UHFFFAOYSA-N 2-ethoxypropane Chemical compound CCOC(C)C XSJVWZAETSBXKU-UHFFFAOYSA-N 0.000 description 2
- STBXJICNOLFPCU-UHFFFAOYSA-N 2-ethyl-4-methoxy-2-methoxycarbonyl-4-oxobutanoic acid Chemical compound COC(=O)C(CC)(C(O)=O)CC(=O)OC STBXJICNOLFPCU-UHFFFAOYSA-N 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- RQRMKMRFKZIYOG-UHFFFAOYSA-N 3-[(6-chloropyridin-3-yl)methyl-methylamino]-2h-furan-5-one Chemical compound C=1C(=O)OCC=1N(C)CC1=CC=C(Cl)N=C1 RQRMKMRFKZIYOG-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- UCTNTYHJFWMUBD-UHFFFAOYSA-N 4-chloro-3-oxobutanoic acid Chemical compound OC(=O)CC(=O)CCl UCTNTYHJFWMUBD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-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
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- VIHAEDVKXSOUAT-UHFFFAOYSA-N but-2-en-4-olide Chemical compound O=C1OCC=C1 VIHAEDVKXSOUAT-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- GIWLDPURHIORDX-UHFFFAOYSA-N methyl 3-hydroxy-5-oxo-2h-furan-4-carboxylate Chemical compound COC(=O)C1=C(O)COC1=O GIWLDPURHIORDX-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SEQRDAAUNCRFIT-UHFFFAOYSA-N 1,1-dichlorobutane Chemical compound CCCC(Cl)Cl SEQRDAAUNCRFIT-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
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- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Description
R1は、水素、アルキル、ハロアルキル、アルケニル、ハロアルケニル、アルキニル、シクロアルキル、シクロアルキルアルキル、ハロシクロアルキル、アルコキシ、アルコキシアルキル、ハロシクロアルキルアルキル又はアリールアルキルであり;
R2は、アルキル、アリール又はアリールアルキルであり;
Zは、水素、アルカリ金属又はアルカリ土類金属であり;
Aは、ピリド−2−イル若しくはピリド−4−イルであるか、又は、ピリド−3−イル(6位がフッ素、塩素、臭素、メチル、トリフルオロメチル又はトリフルオロメトキシで置換されていてもよい。)であるか、又は、ピリダジン−3−イル(6位が塩素又はメチルで置換されていてもよい。)であるか、又は、ピラジン−3−イルであるか、又は、2−クロロピラジン−5−イルであるか、又は、1,3−チアゾール−5−イル(2位が塩素又はメチルで置換されていてもよい。)であり;
又は、
Aは、ピリミジニル、ピラゾリル、チオフェニル、オキサゾリル、イソオキサゾリル、1,2,4−オキサジアゾリル、イソチアゾリル、1,2,4−トリアゾリル又は1,2,5−チアジアゾリル[ここで、これらは、フッ素、塩素、臭素、シアノ、ニトロ、C1−C4−アルキル(フッ素及び/又は塩素で置換されていてもよい。)、C1−C3−アルキルチオ(フッ素及び/又は塩素で置換されていてもよい。)又はC1−C3−アルキルスルホニル(フッ素及び/又は塩素で置換されていてもよい。)で置換されていてもよい。]であり、
又は、
Aは、
R2は、上記で定義されているとおりであり;
R3は、エチルを除くアルキル、シクロアルキル、ハロアルキル、アリール又はアリールアルキルであり;
R4は、アルキル、シクロアルキル、ハロアルキル、アリール又はアリールアルキルであり;
及び、
Zは、上記で定義されているとおりである。
実施例1
68mLのブチロニトリル中の10.4gのカリウム4−(エトキシカルボニル)−5−オキソ−2,5−ジヒドロフラン−3−オキシドと7.5gのN−[(6−クロロピリジン−3−イル)メチル]−2,2−ジフルオロエチルアミンの懸濁液に、室温で、11.5gの硫酸水素カリウムを添加する。その混合物を90から95℃の温度で3時間撹拌する。次に、その混合物を室温まで冷却し、120mLの水と120mLのジクロロメタンを添加する。有機相を除去し、水相を毎回120mLの塩化メチレンで2回抽出する。有機相を合して濃縮乾固させる。11.4gの4−[[(6−クロロピリジン−3−イル)メチル](2,2−ジフルオロエチル)アミノ]フラン−2(5H)−オンが84%の純度(これは、収率92%に相当する。)で得られる。
35mLのブチロニトリル中の5gのナトリウム4−(メトキシカルボニル)−5−オキソ−2,5−ジヒドロフラン−3−オキシドと4.2gのN−[(6−クロロピリジン−3−イル)メチル]−2,2−ジフルオロエチルアミンの懸濁液に、室温で、7.5gの硫酸水素カリウムを添加する。その混合物を90℃の温度で3時間撹拌する。次に、その混合物を室温まで冷却し、60mLの水及び60mLのジクロロメタンと混合させる。有機相を除去し、水相を毎回30mLの塩化メチレンで2回抽出する。有機相を合して濃縮乾固させる。5.95gの4−[[(6−クロロピリジン−3−イル)メチル](2,2−ジフルオロエチル)アミノ]フラン−2(5H)−オンが89%の純度(これは、収率91%に相当する。)で得られる。
35mLのブチロニトリル中の10gのナトリウム4−(メトキシカルボニル)−5−オキソ−2,5−ジヒドロフラン−3−オキシドとナトリウム4−(エトキシカルボニル)−5−オキソ−2,5−ジヒドロフラン−3−オキシド(比率 77:23)及び3.5gのN−[(6−クロロピリジン−3−イル)メチル]メチルアミンの懸濁液に、室温で、7.5gの硫酸水素カリウムを添加する。その混合物を90℃の温度で3時間撹拌する。次に、その混合物を室温まで冷却し、溶媒を完全に除去する。その残渣を50mLの水と混合させ、毎回30mLのジクロロメタンで2回抽出する。有機相を合して濃縮乾固させる。4.7gの4−[[(6−クロロピリジン−3−イル)メチル]メチルアミノ]フラン−2(5H)−オンが95%の純度 (これは、収率82%に相当する。)で得られる。
500mLのジメチルホルムアミド中の78.9gのモノエチルマロン酸カリウムの懸濁液に、35℃で、55gのクロロ酢酸メチルを滴下して加え、得られた混合物を35℃で8時間撹拌する。減圧下に溶媒を除去し、その残渣を100mLの水及び100mLのトルエンと混合させる。相を分離させ、水相を100mLのトルエンで洗浄する。有機相を合して硫酸マグネシウムで脱水し、減圧下に濃縮する。77.6gの2−メトキシ−2−オキソエチルプロパンジカルボン酸メチルが98%の純度(これは、収率80%に相当する。)で得られる。
1H NMR(CDCl3,298K)δ: 3.51s(2H),3.77s(3H),3.78s(3H),4.69s(2H)。
19.6gの2−メトキシ−2−オキソエチルプロパンジカルボン酸メチルに、40℃で、メタノール中の30%ナトリウムメトキシド18gを滴下して加え、得られた混合物を3時間加熱還流する。次に、その混合物を室温まで冷却する。固体を吸引濾過し、20mLのメタノールで洗浄する。生成物を減圧下に50℃で乾燥させる。15.6gのナトリウム4−(メトキシカルボニル)−5−オキソ−2,5−ジヒドロフラン−3−オキシドが99.9%の純度(これは、収率87%に相当する。)で得られる。
1H NMR(D2O,298K)δ: 3.73s(3H),4.42s(2H)。
23.1gの2−エトキシ−2−オキソエチルプロパンジカルボン酸エチルに、40℃で、メタノール中の30%ナトリウムメトキシド18gを滴下して加え、得られた混合物を2時間加熱還流する。次に、その混合物を0℃まで冷却する。固体を吸引濾過し、10mLのメタノールで洗浄する。生成物を減圧下に50℃で乾燥させる。15.7gのナトリウム4−(メトキシカルボニル)−5−オキソ−2,5−ジヒドロフラン−3−オキシドとナトリウム4−(エトキシカルボニル)−5−オキソ−2,5−ジヒドロフラン−3−オキシドの混合物(比率 77:23)が得られる(これは、収率86%に相当する。)。
70mLのブチロニトリル中の5.2gの4−(メトキシカルボニル)−5−オキソ−2,5−ジヒドロフラン−3−オールと5gのN−[(6−クロロピリジン−3−イル)メチル]−2,2−ジフルオロエチルアミンの懸濁液に、室温で、4.5gの硫酸水素カリウムを添加する。その混合物を120℃の温度で3時間撹拌する。次に、その混合物を室温まで冷却し、60mLの水及び60mLのジクロロメタンと混合させる。有機相を除去し、水相を毎回30mLの塩化メチレンで2回抽出する。有機相を合して濃縮乾固させる。7.6gの4−[[(6−クロロピリジン−3−イル)メチル](2,2−ジフルオロエチル)アミノ]フラン−2(5H)−オンが85%の純度(これは、収率94%に相当する。)で得られる。
210mLのブチロニトリル中の18gの4−(メトキシカルボニル)−5−オキソ−2,5−ジヒドロフラン−3−オールと15gのN−[(6−クロロピリジン−3−イル)メチル]メチルアミンの懸濁液に、室温で、16gの硫酸水素カリウムを添加する。その混合物を115℃の温度で5時間撹拌する。次に、その混合物を室温まで冷却し、150mLの水及び70mLのジクロロメタンと混合させる。有機相を除去し、水相を毎回70mLの塩化メチレンで2回抽出する。有機相を合して濃縮乾固させる。24gの4−[[(6−クロロピリジン−3−イル)メチル](メチル)アミノ]フラン−2(5H)−オンが88%の純度(これは、収率92%に相当する。)で得られる。
Claims (6)
- 一般式(I):
一般式(II)
R1は、水素、アルキル、ハロアルキル、アルケニル、ハロアルケニル、アルキニル、シクロアルキル、シクロアルキルアルキル、ハロシクロアルキル、アルコキシ、アルコキシアルキル、ハロシクロアルキルアルキル又はアリールアルキルであり;
R2は、アルキル、アリール又はアリールアルキルであり;
Zは、水素、アルカリ金属又はアルカリ土類金属であり;
Aは、ピリド−2−イル若しくはピリド−4−イルであるか、又は、ピリド−3−イル(6位がフッ素、塩素、臭素、メチル、トリフルオロメチル又はトリフルオロメトキシで置換されていてもよい。)であるか、又は、ピリダジン−3−イル(6位が塩素又はメチルで置換されていてもよい。)であるか、又は、ピラジン−3−イルであるか、又は、2−クロロピラジン−5−イルであるか、又は、1,3−チアゾール−5−イル(2位が塩素又はメチルで置換されていてもよい。)であり;
又は、
Aは、ピリミジニル、ピラゾリル、チオフェニル、オキサゾリル、イソオキサゾリル、1,2,4−オキサジアゾリル、イソチアゾリル、1,2,4−トリアゾリル又は1,2,5−チアジアゾリル[フッ素、塩素、臭素、シアノ、ニトロ、C1−C4−アルキル(フッ素及び/又は塩素で置換されていてもよい。)、C1−C3−アルキルチオ(フッ素及び/又は塩素で置換されていてもよい。)又はC1−C3−アルキルスルホニル(フッ素及び/又は塩素で置換されていてもよい。)で置換されていてもよい。]であり、
又は、
Aは、
Xは、ハロゲン、アルキル又はハロアルキルであり;
Yは、ハロゲン、アルキル、ハロアルキル、ハロアルコキシ、アジド又はシアノである。]
である。〕。
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EP07116639.1 | 2007-09-18 | ||
EP07116639A EP2042496A1 (de) | 2007-09-18 | 2007-09-18 | Verfahren zur Herstellung von 4-Aminobut-2-enoliden |
PCT/EP2008/007270 WO2009036899A1 (de) | 2007-09-18 | 2008-09-05 | Verfahren zur herstellung von 4-aminobut-2-enoliden |
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JP2011500513A JP2011500513A (ja) | 2011-01-06 |
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US (2) | US8273904B2 (ja) |
EP (2) | EP2042496A1 (ja) |
JP (1) | JP5611043B2 (ja) |
KR (1) | KR101516606B1 (ja) |
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EP2230237A1 (de) | 2009-03-16 | 2010-09-22 | Bayer CropScience AG | Neues Verfahren zur Herstellung von Enaminocarbonyl-Verbindungen |
EP2230236A1 (de) | 2009-03-16 | 2010-09-22 | Bayer CropScience AG | Neues Verfahren zur Herstellung von Enaminocarbonyl-Verbindungen |
JP5686805B2 (ja) * | 2009-08-11 | 2015-03-18 | バイエル・クロップサイエンス・アーゲーBayer Cropscience Ag | 2,4−ジオキソテトラヒドロフラン−3−カルボキシラートを調製するための方法 |
TW201111370A (en) * | 2009-08-18 | 2011-04-01 | Bayer Cropscience Ag | Novel process for the preparation of 4-aminobut-2-enolides |
KR20120102060A (ko) | 2009-10-26 | 2012-09-17 | 바이엘 크롭사이언스 아게 | 4-〔〔(6-클로로피리딘-3-일)메틸〕(2,2-디플루오로에틸)아미노〕푸란-2(5h)-온의 신규 고체형 |
US20120252766A1 (en) | 2009-10-27 | 2012-10-04 | Bayer Itechnology Services Gmbh | Co-crystal of 4-furan-2(5h)-one with salicylic acid and use thereof as pesticide |
US20120270904A1 (en) | 2009-10-27 | 2012-10-25 | Bayer Technology Services Gmbh | Co-crystal of 4-furan-2(5h)-one with oxalic acid and use thereof as pesticide |
CN102712630A (zh) * | 2009-10-27 | 2012-10-03 | 拜尔技术服务有限责任公司 | 4-{[(6-氯吡啶-3-基)甲基](2,2-二氟乙基)-氨基}呋喃-2(5h)-酮与苯甲酸的共结晶及其作为杀虫剂的用途 |
KR101721222B1 (ko) * | 2009-12-23 | 2017-03-29 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 4-알콕시푸란-2(5h)-온 또는 4-아릴알콕시푸란-2(5h)-온으로부터 4-아미노부트-2-에놀라이드의 신규 제조방법 |
BR112013014277A2 (pt) * | 2010-12-09 | 2016-07-19 | Bayer Ip Gmbh | misturas pesticidas com propriedades aperfeiçoadas |
CN103347388A (zh) * | 2010-12-09 | 2013-10-09 | 拜耳知识产权有限责任公司 | 具有改善的性能的杀虫剂混合物 |
BR112013022280B8 (pt) * | 2011-03-03 | 2021-06-08 | Bayer Ip Gmbh | processo para a preparação de sals de sódlo ou de potássio de ésteres 4-hidroxi-2-oxo-2,5-dihidrofurano-3-carboxílicos |
US9139547B2 (en) | 2012-08-01 | 2015-09-22 | Bayer Cropscience Ag | Multistage process for preparing alkali metal salts of specific 4-hydroxy-2-oxo-2,5-dihydrofuran-3-carboxylic esters |
CN105503708B (zh) * | 2016-01-26 | 2018-05-29 | 南开大学 | 一类含二氟乙基的杂环化合物及其制备方法和用途 |
WO2023237444A1 (en) | 2022-06-06 | 2023-12-14 | Bayer Aktiengesellschaft | Agrochemical formulations comprising crystalline form a of 4-[(6-chloro-3-pyridylmethyl)(2,2-difluoroethyl)amino]furan-2(5h)-one |
EP4295683A1 (en) | 2022-06-21 | 2023-12-27 | Bayer Aktiengesellschaft | Agrochemical formulations comprising crystalline form a of 4-[(6-chloro-3-pyridylmethyl)(2,2-difluoroethyl)amino]furan-2(5h)-one |
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DE3311003A1 (de) | 1983-03-25 | 1984-09-27 | Bayer Ag, 5090 Leverkusen | Chromon- und thiochromonsubstituierte 1,4-dihydropyridinlactone, mehrere verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
CH658056A5 (de) | 1984-02-09 | 1986-10-15 | Lonza Ag | Verfahren zur herstellung von tetronsaeure. |
US5010176A (en) | 1988-11-10 | 1991-04-23 | Eli Lilly And Company | Antibody-drug conjugates |
EP0539588A1 (en) * | 1990-07-05 | 1993-05-05 | Nippon Soda Co., Ltd. | Amine derivative |
JPH054966A (ja) * | 1990-07-05 | 1993-01-14 | Nippon Soda Co Ltd | アミン誘導体、その製法及び殺虫剤 |
DE102006015468A1 (de) | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | Substituierte Enaminocarbonylverbindungen |
DE102006015467A1 (de) | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | Substituierte Enaminocarbonylverbindungen |
DE102006015470A1 (de) | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | Substituierte Enaminocarbonylverbindungen |
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BRPI0816911A2 (pt) | 2015-03-17 |
CN102775305A (zh) | 2012-11-14 |
EP2042496A1 (de) | 2009-04-01 |
ES2612058T3 (es) | 2017-05-11 |
US9550745B2 (en) | 2017-01-24 |
CN101801948B (zh) | 2013-10-30 |
IL203761A (en) | 2015-09-24 |
JP2011500513A (ja) | 2011-01-06 |
MX2010001963A (es) | 2010-03-10 |
US20100190990A1 (en) | 2010-07-29 |
TWI432419B (zh) | 2014-04-01 |
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KR101516606B1 (ko) | 2015-04-30 |
US8273904B2 (en) | 2012-09-25 |
CN101801948A (zh) | 2010-08-11 |
TW200920741A (en) | 2009-05-16 |
WO2009036899A1 (de) | 2009-03-26 |
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