NO873432L - Fremgangsmaate for fremstilling av imidazolforbindelser. - Google Patents

Info

Publication number

NO873432L

NO873432L NO873432A NO873432A NO873432L NO 873432 L NO873432 L NO 873432L NO 873432 A NO873432 A NO 873432A NO 873432 A NO873432 A NO 873432A NO 873432 L NO873432 L NO 873432L

Authority

NO

Norway

Prior art keywords

pyridyl

methyl

nujol

melting point

imidazole

Prior art date

1986-08-15

Links

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• 238000000034 method Methods 0.000 title claims description 35
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title description 50
• 238000002360 preparation method Methods 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims description 81
• -1 nitro, amino, substituted amino, hydroxy Chemical group 0.000 claims description 75
• 150000003839 salts Chemical class 0.000 claims description 62
• 125000003545 alkoxy group Chemical group 0.000 claims description 61
• 238000006243 chemical reaction Methods 0.000 claims description 52
• 229910052736 halogen Inorganic materials 0.000 claims description 31
• 150000002367 halogens Chemical class 0.000 claims description 31
• 125000003118 aryl group Chemical group 0.000 claims description 27
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
• 125000000217 alkyl group Chemical group 0.000 claims description 23
• 125000004442 acylamino group Chemical group 0.000 claims description 16
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 230000008569 process Effects 0.000 claims description 9
• 125000001424 substituent group Chemical group 0.000 claims description 9
• 125000003282 alkyl amino group Chemical group 0.000 claims description 8
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 229910021529 ammonia Inorganic materials 0.000 claims description 6
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 5
• 239000001257 hydrogen Substances 0.000 claims description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• 125000002252 acyl group Chemical group 0.000 claims description 4
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 238000003379 elimination reaction Methods 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
• 238000005804 alkylation reaction Methods 0.000 claims description 2
• 230000008030 elimination Effects 0.000 claims description 2
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
• 125000001475 halogen functional group Chemical group 0.000 claims 2
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
• 238000002844 melting Methods 0.000 description 281
• 230000008018 melting Effects 0.000 description 281
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
• 238000001819 mass spectrum Methods 0.000 description 78
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
• 239000000203 mixture Substances 0.000 description 68
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 54
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
• 239000000243 solution Substances 0.000 description 42
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
• 150000002460 imidazoles Chemical class 0.000 description 26
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
• 239000002904 solvent Substances 0.000 description 22
• 238000001816 cooling Methods 0.000 description 16
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 238000000354 decomposition reaction Methods 0.000 description 15
• 239000002244 precipitate Substances 0.000 description 15
• 238000012360 testing method Methods 0.000 description 15
• 235000011054 acetic acid Nutrition 0.000 description 14
• 239000011541 reaction mixture Substances 0.000 description 14
• 239000002253 acid Substances 0.000 description 13
• 238000001914 filtration Methods 0.000 description 13
• 238000006722 reduction reaction Methods 0.000 description 13
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 12
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 12
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
• LDLJPVOBMJSVFC-UHFFFAOYSA-N 2-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)aniline Chemical compound CC=1N=C(C=2C(=CC=CC=2)N)NC=1C1=CC=CN=C1 LDLJPVOBMJSVFC-UHFFFAOYSA-N 0.000 description 10
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
• 238000010531 catalytic reduction reaction Methods 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 239000003054 catalyst Substances 0.000 description 9
• 239000003638 chemical reducing agent Substances 0.000 description 9
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
• 239000000741 silica gel Substances 0.000 description 9
• 229910002027 silica gel Inorganic materials 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• 229910052783 alkali metal Inorganic materials 0.000 description 8
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
• 238000010438 heat treatment Methods 0.000 description 8
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• 230000002411 adverse Effects 0.000 description 7
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
• 235000011114 ammonium hydroxide Nutrition 0.000 description 6
• 239000002585 base Substances 0.000 description 6
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
• 235000019341 magnesium sulphate Nutrition 0.000 description 6
• FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 6
• 230000009467 reduction Effects 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• SZWIBPZNNPKBKB-UHFFFAOYSA-N 3-[2-(2-methoxy-4-methylsulfanylphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(SC)=CC=C1C1=NC(C=2C=NC=CC=2)=C(C)N1 SZWIBPZNNPKBKB-UHFFFAOYSA-N 0.000 description 5
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
• 238000004440 column chromatography Methods 0.000 description 5
• 239000000706 filtrate Substances 0.000 description 5
• 210000002683 foot Anatomy 0.000 description 5
• 239000007788 liquid Substances 0.000 description 5
• 150000007522 mineralic acids Chemical class 0.000 description 5
• GZMDJFGGSUILDA-UHFFFAOYSA-N n-[2-chloro-5-methoxy-4-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]acetamide Chemical compound COC1=CC(NC(C)=O)=C(Cl)C=C1C1=NC(C=2C=NC=CC=2)=C(C)N1 GZMDJFGGSUILDA-UHFFFAOYSA-N 0.000 description 5
• 150000007524 organic acids Chemical class 0.000 description 5
• 239000012074 organic phase Substances 0.000 description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 235000011181 potassium carbonates Nutrition 0.000 description 5
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
• 229910052938 sodium sulfate Inorganic materials 0.000 description 5
• 235000011152 sodium sulphate Nutrition 0.000 description 5
• 238000010998 test method Methods 0.000 description 5
• VXYIFBJCMQUFME-UHFFFAOYSA-N 1-hydroxyimino-1-pyridin-3-ylpropan-2-one Chemical compound CC(=O)C(=NO)C1=CC=CN=C1 VXYIFBJCMQUFME-UHFFFAOYSA-N 0.000 description 4
• JTMQPIWQTLVTLP-UHFFFAOYSA-N 2-chloro-4-methoxy-5-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)aniline Chemical compound COC1=CC(Cl)=C(N)C=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 JTMQPIWQTLVTLP-UHFFFAOYSA-N 0.000 description 4
• IEXWFKFVMYTVKZ-UHFFFAOYSA-N 2-chloro-5-methoxy-n-methyl-4-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)aniline Chemical compound C1=C(Cl)C(NC)=CC(OC)=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 IEXWFKFVMYTVKZ-UHFFFAOYSA-N 0.000 description 4
• AVNRKEGUSALBSN-UHFFFAOYSA-N 3-[2-(2,4-dimethoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(OC)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 AVNRKEGUSALBSN-UHFFFAOYSA-N 0.000 description 4
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
• 150000001340 alkali metals Chemical class 0.000 description 4
• 239000012267 brine Substances 0.000 description 4
• 238000001704 evaporation Methods 0.000 description 4
• 230000008020 evaporation Effects 0.000 description 4
• 235000019253 formic acid Nutrition 0.000 description 4
• 230000002140 halogenating effect Effects 0.000 description 4
• 229910052742 iron Inorganic materials 0.000 description 4
• 229910052751 metal Inorganic materials 0.000 description 4
• 239000002184 metal Substances 0.000 description 4
• VDLSGWABQRFJOZ-UHFFFAOYSA-N n-[2-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 VDLSGWABQRFJOZ-UHFFFAOYSA-N 0.000 description 4
• UQPXJHUMNXDDGA-UHFFFAOYSA-N n-[3-methoxy-4-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]acetamide Chemical compound COC1=CC(NC(C)=O)=CC=C1C1=NC(C=2C=NC=CC=2)=C(C)N1 UQPXJHUMNXDDGA-UHFFFAOYSA-N 0.000 description 4
• 238000006386 neutralization reaction Methods 0.000 description 4
• 239000003960 organic solvent Substances 0.000 description 4
• 235000019260 propionic acid Nutrition 0.000 description 4
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
• 208000010110 spontaneous platelet aggregation Diseases 0.000 description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
• OEXRZZMPNACKSP-UHFFFAOYSA-N 1-methyl-3-[2-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]thiourea Chemical compound CNC(=S)NC1=CC=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 OEXRZZMPNACKSP-UHFFFAOYSA-N 0.000 description 3
• IFTYKUALNOLUPZ-UHFFFAOYSA-N 1-methyl-3-[2-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]urea Chemical compound CNC(=O)NC1=CC=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 IFTYKUALNOLUPZ-UHFFFAOYSA-N 0.000 description 3
• BXLCAZBQEADHJQ-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)-5-ethyl-1h-imidazol-4-yl]pyridine Chemical compound CCC=1NC(C=2C=C(OC)C(OC)=CC=2)=NC=1C1=CC=CC=N1 BXLCAZBQEADHJQ-UHFFFAOYSA-N 0.000 description 3
• GIBXUWRWLXXVEJ-UHFFFAOYSA-N 3-[2-(2,4-dimethoxyphenyl)-5-ethyl-1h-imidazol-4-yl]pyridine Chemical compound CCC=1N=C(C=2C(=CC(OC)=CC=2)OC)NC=1C1=CC=CN=C1 GIBXUWRWLXXVEJ-UHFFFAOYSA-N 0.000 description 3
• KORRLLBRODMOKX-UHFFFAOYSA-N 3-[2-(2-fluorophenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound CC=1N=C(C=2C(=CC=CC=2)F)NC=1C1=CC=CN=C1 KORRLLBRODMOKX-UHFFFAOYSA-N 0.000 description 3
• LZZKPPHJWYRXKH-UHFFFAOYSA-N 3-[2-(2-methoxy-4-methylsulfinylphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(S(C)=O)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 LZZKPPHJWYRXKH-UHFFFAOYSA-N 0.000 description 3
• CHFSSUXKCICDPZ-UHFFFAOYSA-N 3-[2-(2-methoxy-4-methylsulfonylphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(S(C)(=O)=O)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 CHFSSUXKCICDPZ-UHFFFAOYSA-N 0.000 description 3
• LAXFXVCOZXSTQL-UHFFFAOYSA-N 3-[2-(2-methoxy-4-phenylmethoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound C=1C=C(C=2NC(=C(C)N=2)C=2C=NC=CC=2)C(OC)=CC=1OCC1=CC=CC=C1 LAXFXVCOZXSTQL-UHFFFAOYSA-N 0.000 description 3
• QVNXLVKVZJSJMC-UHFFFAOYSA-N 3-[2-(2-methoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC=CC=C1C1=NC(C=2C=NC=CC=2)=C(C)N1 QVNXLVKVZJSJMC-UHFFFAOYSA-N 0.000 description 3
• QRPGPBXSILZFFP-UHFFFAOYSA-N 3-[2-(4-chloro-2-methoxy-5-nitrophenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(Cl)=C([N+]([O-])=O)C=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 QRPGPBXSILZFFP-UHFFFAOYSA-N 0.000 description 3
• VORQOUQLEKZGIZ-UHFFFAOYSA-N 3-[2-(4-chloro-2-methoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(Cl)=CC=C1C1=NC(C=2C=NC=CC=2)=C(C)N1 VORQOUQLEKZGIZ-UHFFFAOYSA-N 0.000 description 3
• YJNFQAGBTGGRDN-UHFFFAOYSA-N 3-[2-(5-bromo-2,4-dimethoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound C1=C(Br)C(OC)=CC(OC)=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 YJNFQAGBTGGRDN-UHFFFAOYSA-N 0.000 description 3
• NQYSBVGHSRVVJW-UHFFFAOYSA-N 3-[5-methyl-2-(2-nitrophenyl)-1h-imidazol-4-yl]pyridine Chemical compound CC=1N=C(C=2C(=CC=CC=2)[N+]([O-])=O)NC=1C1=CC=CN=C1 NQYSBVGHSRVVJW-UHFFFAOYSA-N 0.000 description 3
• AZGSDCUHMZSAGB-UHFFFAOYSA-N 3-methoxy-4-(5-methyl-4-pyridin-3-yl-1H-imidazol-2-yl)phenol Chemical compound COC1=CC(O)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 AZGSDCUHMZSAGB-UHFFFAOYSA-N 0.000 description 3
• PBFMYDIMFVZMLC-UHFFFAOYSA-N 3-methoxy-4-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)aniline Chemical compound COC1=CC(N)=CC=C1C1=NC(C=2C=NC=CC=2)=C(C)N1 PBFMYDIMFVZMLC-UHFFFAOYSA-N 0.000 description 3
• IIDYLOIANVDZJH-UHFFFAOYSA-N 4-[2-(2,4-dimethoxyphenyl)-5-ethyl-1h-imidazol-4-yl]pyridine Chemical compound CCC=1NC(C=2C(=CC(OC)=CC=2)OC)=NC=1C1=CC=NC=C1 IIDYLOIANVDZJH-UHFFFAOYSA-N 0.000 description 3
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