LU82342A1 - Procede de preparation de 2-aminopyrazines substituees - Google Patents
Procede de preparation de 2-aminopyrazines substituees Download PDFInfo
- Publication number
- LU82342A1 LU82342A1 LU82342A LU82342A LU82342A1 LU 82342 A1 LU82342 A1 LU 82342A1 LU 82342 A LU82342 A LU 82342A LU 82342 A LU82342 A LU 82342A LU 82342 A1 LU82342 A1 LU 82342A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- acid
- approximately
- mixture
- hydroxyimino
- chloro
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 38
- 230000008569 process Effects 0.000 title claims description 17
- 239000000203 mixture Substances 0.000 claims description 50
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 32
- 239000011541 reaction mixture Substances 0.000 claims description 27
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 21
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 20
- 238000003756 stirring Methods 0.000 claims description 19
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 claims description 18
- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical class NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 claims description 17
- YURQPGVFJJHBCK-UHFFFAOYSA-N 1-cyano-n'-hydroxymethanimidamide Chemical compound ON=C(N)C#N YURQPGVFJJHBCK-UHFFFAOYSA-N 0.000 claims description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 12
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- SRANPMHVZAXTBA-UHFFFAOYSA-N n-(cyanomethyl)nitrous amide Chemical compound O=NNCC#N SRANPMHVZAXTBA-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- 150000002923 oximes Chemical class 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002516 radical scavenger Substances 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- QFPYWIXREIQTOD-UHFFFAOYSA-N 2-amino-4-hydroxybutanenitrile Chemical compound N#CC(N)CCO QFPYWIXREIQTOD-UHFFFAOYSA-N 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 37
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 238000005303 weighing Methods 0.000 description 33
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000000243 solution Substances 0.000 description 26
- 239000004157 Nitrosyl chloride Substances 0.000 description 21
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 21
- 235000019392 nitrosyl chloride Nutrition 0.000 description 21
- 238000007363 ring formation reaction Methods 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 19
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000007789 gas Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- -1 3,5-disubstituted 2-amino-pyrazine-l-oxides Chemical class 0.000 description 11
- XFKYKTBPRBZDFG-UHFFFAOYSA-N 2-aminoacetonitrile;hydrochloride Chemical compound Cl.NCC#N XFKYKTBPRBZDFG-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000002274 desiccant Substances 0.000 description 9
- 238000001819 mass spectrum Methods 0.000 description 9
- 235000011007 phosphoric acid Nutrition 0.000 description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000538 analytical sample Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 150000003440 styrenes Chemical class 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- DBASWHONNARUPG-UHFFFAOYSA-N 1,2-dichloro-4-prop-1-enylbenzene Chemical compound CC=CC1=CC=C(Cl)C(Cl)=C1 DBASWHONNARUPG-UHFFFAOYSA-N 0.000 description 3
- SMYHFDLFOKKDOO-UHFFFAOYSA-N 1-(2-bromophenyl)propan-1-ol Chemical compound CCC(O)C1=CC=CC=C1Br SMYHFDLFOKKDOO-UHFFFAOYSA-N 0.000 description 3
- NTTBDWAXCRRVJY-UHFFFAOYSA-N 1-(4-ethylphenyl)propan-1-ol Chemical compound CCC(O)C1=CC=C(CC)C=C1 NTTBDWAXCRRVJY-UHFFFAOYSA-N 0.000 description 3
- XCHPVOMIGFUUPS-UHFFFAOYSA-N 2-[[1-(4-bromophenyl)-2-hydroxyiminopropyl]amino]acetonitrile Chemical compound N#CCNC(C(=NO)C)C1=CC=C(Br)C=C1 XCHPVOMIGFUUPS-UHFFFAOYSA-N 0.000 description 3
- NFFWTXKHMBVZFK-UHFFFAOYSA-N 6-methyl-5-phenylpyrazin-2-amine Chemical compound CC1=NC(N)=CN=C1C1=CC=CC=C1 NFFWTXKHMBVZFK-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QROGIFZRVHSFLM-QHHAFSJGSA-N [(e)-prop-1-enyl]benzene Chemical compound C\C=C\C1=CC=CC=C1 QROGIFZRVHSFLM-QHHAFSJGSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- JIMRVZGQHAUYPJ-UHFFFAOYSA-N n-(1-chloro-1-phenylpropan-2-ylidene)hydroxylamine Chemical compound ON=C(C)C(Cl)C1=CC=CC=C1 JIMRVZGQHAUYPJ-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- PJYGECCAJOYJMK-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)propan-1-ol Chemical compound CCC(O)C1=CC=C(Cl)C(Cl)=C1 PJYGECCAJOYJMK-UHFFFAOYSA-N 0.000 description 2
- VGQRIILEZYZAOE-UHFFFAOYSA-N 1-(4-ethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(CC)C=C1 VGQRIILEZYZAOE-UHFFFAOYSA-N 0.000 description 2
- IPDBNWOEFLIODE-UHFFFAOYSA-N 1-bromo-2-prop-1-enylbenzene Chemical compound CC=CC1=CC=CC=C1Br IPDBNWOEFLIODE-UHFFFAOYSA-N 0.000 description 2
- KZNLLGVHMGYUAX-UHFFFAOYSA-N 1-bromo-4-prop-1-enylbenzene Chemical compound CC=CC1=CC=C(Br)C=C1 KZNLLGVHMGYUAX-UHFFFAOYSA-N 0.000 description 2
- MKJOTWMWLNTTJM-UHFFFAOYSA-N 1-ethyl-4-prop-1-enylbenzene Chemical group CCC1=CC=C(C=CC)C=C1 MKJOTWMWLNTTJM-UHFFFAOYSA-N 0.000 description 2
- MNEUEZGHHHVQCY-UHFFFAOYSA-N 2-[[1-(2,4-dimethylphenyl)-2-hydroxyiminopropyl]amino]acetonitrile Chemical compound N#CCNC(C(=NO)C)C1=CC=C(C)C=C1C MNEUEZGHHHVQCY-UHFFFAOYSA-N 0.000 description 2
- BMFQKUNPFUBRJH-UHFFFAOYSA-N 2-[[1-(2-bromophenyl)-2-hydroxyiminopropyl]amino]acetonitrile Chemical compound N#CCNC(C(=NO)C)C1=CC=CC=C1Br BMFQKUNPFUBRJH-UHFFFAOYSA-N 0.000 description 2
- QHBJNPWYPLXNSI-UHFFFAOYSA-N 2-[[1-(4-ethylphenyl)-2-hydroxyiminopropyl]amino]acetonitrile Chemical compound CCC1=CC=C(C(NCC#N)C(C)=NO)C=C1 QHBJNPWYPLXNSI-UHFFFAOYSA-N 0.000 description 2
- NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 description 2
- XESMERCPCQXGAI-UHFFFAOYSA-N 2-hydroxyiminoacetonitrile Chemical compound ON=CC#N XESMERCPCQXGAI-UHFFFAOYSA-N 0.000 description 2
- ZWUSBSHBFFPRNE-UHFFFAOYSA-N 3,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1Cl ZWUSBSHBFFPRNE-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- DOHFKSNTLLOMIX-UHFFFAOYSA-N 5-(2,4-dimethylphenyl)-6-methylpyrazin-2-amine Chemical compound CC1=CC(C)=CC=C1C1=NC=C(N)N=C1C DOHFKSNTLLOMIX-UHFFFAOYSA-N 0.000 description 2
- SPYWXUDZRSBABN-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)-6-methylpyrazin-2-amine Chemical compound CC1=NC(N)=CN=C1C1=CC=C(Cl)C(Cl)=C1 SPYWXUDZRSBABN-UHFFFAOYSA-N 0.000 description 2
- RIKLWNXUCIOIPI-UHFFFAOYSA-N 5-(3-bromophenyl)-6-methylpyrazin-2-amine Chemical compound CC1=NC(N)=CN=C1C1=CC=CC(Br)=C1 RIKLWNXUCIOIPI-UHFFFAOYSA-N 0.000 description 2
- QYCWZGDAYYKQTL-UHFFFAOYSA-N 5-(4-bromophenyl)-6-ethylpyrazin-2-amine Chemical compound CCC1=NC(N)=CN=C1C1=CC=C(Br)C=C1 QYCWZGDAYYKQTL-UHFFFAOYSA-N 0.000 description 2
- SJYCYRJOUJAQFB-UHFFFAOYSA-N 5-(4-bromophenyl)-6-methylpyrazin-2-amine Chemical compound CC1=NC(N)=CN=C1C1=CC=C(Br)C=C1 SJYCYRJOUJAQFB-UHFFFAOYSA-N 0.000 description 2
- JGNQFJDHMNVADD-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-methylpyrazin-2-amine Chemical compound CC1=NC(N)=CN=C1C1=CC=C(Cl)C=C1 JGNQFJDHMNVADD-UHFFFAOYSA-N 0.000 description 2
- YWJPZSPKFLCFRU-UHFFFAOYSA-N 5-(4-ethylphenyl)-6-methylpyrazin-2-amine Chemical compound C1=CC(CC)=CC=C1C1=NC=C(N)N=C1C YWJPZSPKFLCFRU-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- YKGPLGQFEQISRN-UHFFFAOYSA-N CCC(=NO)C(Cl)C1=CC=C(Br)C=C1 Chemical compound CCC(=NO)C(Cl)C1=CC=C(Br)C=C1 YKGPLGQFEQISRN-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- XHDBQDSIMYOXBU-UHFFFAOYSA-N N-[1-chloro-1-(2,4-dimethylphenyl)propan-2-ylidene]hydroxylamine Chemical compound ON=C(C)C(Cl)C1=CC=C(C)C=C1C XHDBQDSIMYOXBU-UHFFFAOYSA-N 0.000 description 2
- HEHVCMHKHXZXLJ-UHFFFAOYSA-N N-[1-chloro-1-(4-chlorophenyl)propan-2-ylidene]hydroxylamine Chemical compound ON=C(C)C(Cl)C1=CC=C(Cl)C=C1 HEHVCMHKHXZXLJ-UHFFFAOYSA-N 0.000 description 2
- WKDONNWGGRKJBQ-UHFFFAOYSA-N N-[1-chloro-1-(4-ethylphenyl)propan-2-ylidene]hydroxylamine Chemical compound CCC1=CC=C(C(Cl)C(C)=NO)C=C1 WKDONNWGGRKJBQ-UHFFFAOYSA-N 0.000 description 2
- OCAAIVJYAVLKHY-UHFFFAOYSA-N ON=C(C)C(Cl)C1=CC=C(Br)C=C1 Chemical compound ON=C(C)C(Cl)C1=CC=C(Br)C=C1 OCAAIVJYAVLKHY-UHFFFAOYSA-N 0.000 description 2
- MIGIDHDRZQLPBH-UHFFFAOYSA-N ON=C(C)C(Cl)C1=CC=CC(Br)=C1 Chemical compound ON=C(C)C(Cl)C1=CC=CC(Br)=C1 MIGIDHDRZQLPBH-UHFFFAOYSA-N 0.000 description 2
- ZIUMYUZJGDWWAP-UHFFFAOYSA-N ON=C(C)C(Cl)C1=CC=CC=C1Br Chemical compound ON=C(C)C(Cl)C1=CC=CC=C1Br ZIUMYUZJGDWWAP-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003195 pteridines Chemical class 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 150000003216 pyrazines Chemical class 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- QCDHDMNVZBREKZ-UHFFFAOYSA-N 1-bromo-3-prop-1-enylbenzene Chemical compound CC=CC1=CC=CC(Br)=C1 QCDHDMNVZBREKZ-UHFFFAOYSA-N 0.000 description 1
- HAZZRKZNTNNBJW-UHFFFAOYSA-N 1-chloro-4-prop-1-enylbenzene Chemical compound CC=CC1=CC=C(Cl)C=C1 HAZZRKZNTNNBJW-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- CQXMBSOTZBZEPY-UHFFFAOYSA-N 2-[(2-hydroxyimino-1-phenylpropyl)amino]acetonitrile Chemical compound N#CCNC(C(=NO)C)C1=CC=CC=C1 CQXMBSOTZBZEPY-UHFFFAOYSA-N 0.000 description 1
- XXDPCQNZEQSNRO-UHFFFAOYSA-N 2-[[1-(3,4-dichlorophenyl)-2-hydroxyiminopropyl]amino]acetonitrile Chemical compound N#CCNC(C(=NO)C)C1=CC=C(Cl)C(Cl)=C1 XXDPCQNZEQSNRO-UHFFFAOYSA-N 0.000 description 1
- BPIVUWFBHBSDKY-UHFFFAOYSA-N 2-[[1-(3-bromophenyl)-2-hydroxyiminopropyl]amino]acetonitrile Chemical compound N#CCNC(C(=NO)C)C1=CC=CC(Br)=C1 BPIVUWFBHBSDKY-UHFFFAOYSA-N 0.000 description 1
- FRDBUNRHSODPSH-UHFFFAOYSA-N 2-[[1-(4-bromophenyl)-2-hydroxyiminobutyl]amino]acetonitrile Chemical compound N#CCNC(C(=NO)CC)C1=CC=C(Br)C=C1 FRDBUNRHSODPSH-UHFFFAOYSA-N 0.000 description 1
- FEXHUSARWHBPRU-UHFFFAOYSA-N 2-[[1-(4-chlorophenyl)-2-hydroxyiminopropyl]amino]acetonitrile Chemical compound N#CCNC(C(=NO)C)C1=CC=C(Cl)C=C1 FEXHUSARWHBPRU-UHFFFAOYSA-N 0.000 description 1
- FTTWZGSFBWMLSP-UHFFFAOYSA-N 2-[[2-hydroxyimino-1-[3-(trifluoromethyl)phenyl]propyl]amino]acetonitrile Chemical compound N#CCNC(C(=NO)C)C1=CC=CC(C(F)(F)F)=C1 FTTWZGSFBWMLSP-UHFFFAOYSA-N 0.000 description 1
- JRWAUKYINYWSTA-UHFFFAOYSA-N 2-amino-2-cyanoacetamide Chemical compound N#CC(N)C(N)=O JRWAUKYINYWSTA-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical class N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- YOZWFAYEDBGMDN-UHFFFAOYSA-N 4-chloro-3-hydroxyiminobutan-2-one Chemical compound CC(=O)C(CCl)=NO YOZWFAYEDBGMDN-UHFFFAOYSA-N 0.000 description 1
- CFJZQKIGKAJRGB-UHFFFAOYSA-N 5-(2-bromophenyl)-6-methylpyrazin-2-amine Chemical compound CC1=NC(N)=CN=C1C1=CC=CC=C1Br CFJZQKIGKAJRGB-UHFFFAOYSA-N 0.000 description 1
- MZYZCCIXMLNATA-UHFFFAOYSA-N 6-methyl-5-[3-(trifluoromethyl)phenyl]pyrazin-2-amine Chemical compound CC1=NC(N)=CN=C1C1=CC=CC(C(F)(F)F)=C1 MZYZCCIXMLNATA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- UODHLFWPXJGIAL-UHFFFAOYSA-N CCOC(=O)C1=NC(C)=C[N+]([O-])=C1N Chemical compound CCOC(=O)C1=NC(C)=C[N+]([O-])=C1N UODHLFWPXJGIAL-UHFFFAOYSA-N 0.000 description 1
- TWTWFMUQSOFTRN-UHFFFAOYSA-M CC[Mg]Br Chemical compound CC[Mg]Br TWTWFMUQSOFTRN-UHFFFAOYSA-M 0.000 description 1
- 241001245642 Camponotus consobrinus Species 0.000 description 1
- 235000016796 Euonymus japonicus Nutrition 0.000 description 1
- 240000006570 Euonymus japonicus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 101000933374 Gallus gallus Brain-specific homeobox/POU domain protein 3 Proteins 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QHUJDHXLSJCXPS-UHFFFAOYSA-N ON=C(C)C(Cl)C1=CC=C(Cl)C(Cl)=C1 Chemical compound ON=C(C)C(Cl)C1=CC=C(Cl)C(Cl)=C1 QHUJDHXLSJCXPS-UHFFFAOYSA-N 0.000 description 1
- RFBKSILYIMILDS-UHFFFAOYSA-N ON=C(C)C(Cl)C1=CC=CC(C(F)(F)F)=C1 Chemical compound ON=C(C)C(Cl)C1=CC=CC(C(F)(F)F)=C1 RFBKSILYIMILDS-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- KFCUPNHUPHDVJC-UHFFFAOYSA-N bromine azide Chemical compound BrN=[N+]=[N-] KFCUPNHUPHDVJC-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical class OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- JYGRVMQGWVVHJE-UHFFFAOYSA-N ethyl 2-amino-2-cyanoacetate Chemical compound CCOC(=O)C(N)C#N JYGRVMQGWVVHJE-UHFFFAOYSA-N 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002101 lytic effect Effects 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HYRFBZQNFPRBBS-UHFFFAOYSA-N n-carbamoyl-2,6-dichlorobenzamide Chemical class NC(=O)NC(=O)C1=C(Cl)C=CC=C1Cl HYRFBZQNFPRBBS-UHFFFAOYSA-N 0.000 description 1
- BMNDJWSIKZECMH-UHFFFAOYSA-N nitrosyl bromide Chemical compound BrN=O BMNDJWSIKZECMH-UHFFFAOYSA-N 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000029305 taxis Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 230000001549 tubercolostatic effect Effects 0.000 description 1
- 239000000814 tuberculostatic agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/18—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
- C07C33/20—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part monocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
- C07D241/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C11/00—Fermentation processes for beer
- C12C11/02—Pitching yeast
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- Mycology (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2763079 | 1979-04-06 | ||
| US06/027,630 US4211870A (en) | 1979-04-06 | 1979-04-06 | Preparation of substituted 2-aminopyrazines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU82342A1 true LU82342A1 (fr) | 1980-07-02 |
Family
ID=21838837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU82342A LU82342A1 (fr) | 1979-04-06 | 1980-04-04 | Procede de preparation de 2-aminopyrazines substituees |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4211870A (en]) |
| EP (1) | EP0018144A1 (en]) |
| JP (1) | JPS55141473A (en]) |
| KR (1) | KR830002731A (en]) |
| AU (1) | AU5710280A (en]) |
| BE (1) | BE882608A (en]) |
| BR (1) | BR8002079A (en]) |
| CA (1) | CA1157860A (en]) |
| CS (1) | CS215055B2 (en]) |
| DD (1) | DD150057A5 (en]) |
| DK (1) | DK144280A (en]) |
| ES (1) | ES8105303A1 (en]) |
| FI (1) | FI801056A7 (en]) |
| FR (1) | FR2453159A1 (en]) |
| GB (1) | GB2046751A (en]) |
| GR (1) | GR68096B (en]) |
| IL (1) | IL59761A0 (en]) |
| IT (1) | IT1147345B (en]) |
| LU (1) | LU82342A1 (en]) |
| NZ (1) | NZ193345A (en]) |
| PL (1) | PL223264A1 (en]) |
| PT (1) | PT71056A (en]) |
| RO (1) | RO79384A (en]) |
| SU (1) | SU932989A3 (en]) |
| ZA (1) | ZA802005B (en]) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2209465C (en) * | 1996-07-11 | 2008-04-29 | Lonza Ag | Process for preparing 3-alkoxy-5-alkylpyrazin-2-amines |
| EE200200453A (et) * | 2000-02-16 | 2003-12-15 | Neurogen Corporation | Asendatud arüülpürasiinid |
| CA2496197A1 (en) * | 2002-08-20 | 2004-03-04 | Neurogen Corporation | 5-substituted-2-arylpyrazines as modulators of crf receptors |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE794329A (fr) * | 1972-01-20 | 1973-07-19 | Pechiney Ugine Kuhlmann | Derives d'aza-2 butadienes-1,3 et procede pour leur preparation |
| EG11837A (en) * | 1974-09-19 | 1977-12-31 | Lilly Co Eli | Novel 1-(substituted benzoyl)-3-(substituted pyrazinyl ureas used as insecticides |
| US4160834A (en) * | 1977-03-09 | 1979-07-10 | Eli Lilly And Company | 1-(Substituted benzoyl)-3-(substituted pyrazinyl)ureas |
-
1979
- 1979-04-06 US US06/027,630 patent/US4211870A/en not_active Expired - Lifetime
-
1980
- 1980-04-02 PT PT71056A patent/PT71056A/pt unknown
- 1980-04-02 CA CA000349061A patent/CA1157860A/en not_active Expired
- 1980-04-02 CS CS802293A patent/CS215055B2/cs unknown
- 1980-04-02 BR BR8002079A patent/BR8002079A/pt unknown
- 1980-04-02 AU AU57102/80A patent/AU5710280A/en not_active Abandoned
- 1980-04-02 DK DK144280A patent/DK144280A/da unknown
- 1980-04-02 FI FI801056A patent/FI801056A7/fi not_active Application Discontinuation
- 1980-04-02 NZ NZ193345A patent/NZ193345A/xx unknown
- 1980-04-02 FR FR8007457A patent/FR2453159A1/fr not_active Withdrawn
- 1980-04-02 ES ES490287A patent/ES8105303A1/es not_active Expired
- 1980-04-02 GR GR61609A patent/GR68096B/el unknown
- 1980-04-03 IL IL59761A patent/IL59761A0/xx unknown
- 1980-04-03 DD DD80220207A patent/DD150057A5/de unknown
- 1980-04-03 GB GB8011363A patent/GB2046751A/en not_active Withdrawn
- 1980-04-03 BE BE1/9771A patent/BE882608A/fr unknown
- 1980-04-03 ZA ZA00802005A patent/ZA802005B/xx unknown
- 1980-04-03 EP EP80301085A patent/EP0018144A1/en not_active Ceased
- 1980-04-04 RO RO80100722A patent/RO79384A/ro unknown
- 1980-04-04 PL PL22326480A patent/PL223264A1/xx unknown
- 1980-04-04 IT IT21231/80A patent/IT1147345B/it active
- 1980-04-04 KR KR1019800001429A patent/KR830002731A/ko not_active Abandoned
- 1980-04-04 LU LU82342A patent/LU82342A1/fr unknown
- 1980-04-04 SU SU802902455A patent/SU932989A3/ru active
- 1980-04-05 JP JP4511480A patent/JPS55141473A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PL223264A1 (en]) | 1981-01-30 |
| GR68096B (en]) | 1981-10-30 |
| IT1147345B (it) | 1986-11-19 |
| JPS55141473A (en) | 1980-11-05 |
| ES490287A0 (es) | 1981-05-16 |
| US4211870A (en) | 1980-07-08 |
| NZ193345A (en) | 1982-11-23 |
| IT8021231A0 (it) | 1980-04-04 |
| ZA802005B (en) | 1981-11-25 |
| DK144280A (da) | 1980-10-07 |
| FI801056A7 (fi) | 1980-10-07 |
| SU932989A3 (ru) | 1982-05-30 |
| BE882608A (fr) | 1980-10-03 |
| CS215055B2 (en) | 1982-07-30 |
| CA1157860A (en) | 1983-11-29 |
| PT71056A (en) | 1980-05-01 |
| RO79384A (ro) | 1982-06-25 |
| FR2453159A1 (fr) | 1980-10-31 |
| IL59761A0 (en) | 1980-06-30 |
| GB2046751A (en) | 1980-11-19 |
| ES8105303A1 (es) | 1981-05-16 |
| KR830002731A (ko) | 1983-05-30 |
| EP0018144A1 (en) | 1980-10-29 |
| AU5710280A (en) | 1980-10-09 |
| DD150057A5 (de) | 1981-08-12 |
| BR8002079A (pt) | 1980-11-25 |
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