NO872372L - Fremgangsmaate for fremstilling av kondenserte imidazohetero-cykliske forbindelser. - Google Patents

Info

Publication number

NO872372L

NO872372L NO872372A NO872372A NO872372L NO 872372 L NO872372 L NO 872372L NO 872372 A NO872372 A NO 872372A NO 872372 A NO872372 A NO 872372A NO 872372 L NO872372 L NO 872372L

Authority

NO

Norway

Prior art keywords

mol

water

solid

imidazo

room temperature

Prior art date

1986-06-09

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• 238000000034 method Methods 0.000 title claims description 22
• 150000001875 compounds Chemical class 0.000 claims abstract description 148
• -1 hydroxymethylene Chemical group 0.000 claims abstract description 37
• 239000001257 hydrogen Substances 0.000 claims abstract description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
• 239000002253 acid Substances 0.000 claims abstract description 25
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 13
• 150000001408 amides Chemical class 0.000 claims abstract description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
• 150000007513 acids Chemical class 0.000 claims abstract description 6
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
• 150000002367 halogens Chemical class 0.000 claims abstract description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 3
• 150000002148 esters Chemical class 0.000 claims abstract description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
• 229910052757 nitrogen Inorganic materials 0.000 claims description 163
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 160
• 239000002904 solvent Substances 0.000 claims description 54
• 238000004519 manufacturing process Methods 0.000 claims description 50
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 44
• 238000006243 chemical reaction Methods 0.000 claims description 35
• 125000000217 alkyl group Chemical group 0.000 claims description 25
• 150000003839 salts Chemical class 0.000 claims description 21
• 238000010438 heat treatment Methods 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
• 239000002585 base Substances 0.000 claims description 7
• 239000007858 starting material Substances 0.000 claims description 7
• 150000001412 amines Chemical class 0.000 claims description 6
• LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 claims description 6
• AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 5
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 5
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 4
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 4
• 125000000623 heterocyclic group Chemical group 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 3
• 150000004677 hydrates Chemical class 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
• 230000003647 oxidation Effects 0.000 claims description 3
• 238000007254 oxidation reaction Methods 0.000 claims description 3
• 238000005987 sulfurization reaction Methods 0.000 claims description 3
• 239000003637 basic solution Substances 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
• 230000032050 esterification Effects 0.000 claims description 2
• 238000005886 esterification reaction Methods 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims description 2
• 229910052751 metal Inorganic materials 0.000 claims description 2
• 239000002184 metal Substances 0.000 claims description 2
• 230000003287 optical effect Effects 0.000 claims description 2
• 230000001590 oxidative effect Effects 0.000 claims description 2
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 230000001225 therapeutic effect Effects 0.000 claims 1
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
• 230000000694 effects Effects 0.000 abstract description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
• 239000001961 anticonvulsive agent Substances 0.000 abstract description 2
• 239000002249 anxiolytic agent Substances 0.000 abstract description 2
• 239000003158 myorelaxant agent Substances 0.000 abstract description 2
• 150000001298 alcohols Chemical class 0.000 abstract 1
• 229940125681 anticonvulsant agent Drugs 0.000 abstract 1
• 125000002541 furyl group Chemical group 0.000 abstract 1
• 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
• 150000002576 ketones Chemical class 0.000 abstract 1
• 229940035363 muscle relaxants Drugs 0.000 abstract 1
• 125000001544 thienyl group Chemical group 0.000 abstract 1
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 515
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 399
• 239000007787 solid Substances 0.000 description 392
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 372
• 229910001868 water Inorganic materials 0.000 description 367
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 324
• 239000000243 solution Substances 0.000 description 297
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 261
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 259
• 239000011541 reaction mixture Substances 0.000 description 234
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 225
• 238000004458 analytical method Methods 0.000 description 218
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 204
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 159
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 147
• 239000000203 mixture Substances 0.000 description 139
• 239000000706 filtrate Substances 0.000 description 133
• 238000001914 filtration Methods 0.000 description 131
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 126
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 123
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 85
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 78
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 74
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
• 239000000725 suspension Substances 0.000 description 71
• 239000010410 layer Substances 0.000 description 70
• 239000011343 solid material Substances 0.000 description 65
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 64
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 62
• 239000012299 nitrogen atmosphere Substances 0.000 description 58
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 53
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 50
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 50
• 239000003921 oil Substances 0.000 description 50
• 235000019198 oils Nutrition 0.000 description 50
• SAALQYKUFCIMHR-UHFFFAOYSA-N propan-2-ol;2-propan-2-yloxypropane Chemical compound CC(C)O.CC(C)OC(C)C SAALQYKUFCIMHR-UHFFFAOYSA-N 0.000 description 50
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 48
• 239000012065 filter cake Substances 0.000 description 48
• LTCYBYUOSOJSJD-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetic acid Chemical compound N=1C2=CC=CN=C2N(CC(=O)O)C=1C1=CC=C(Cl)C=C1 LTCYBYUOSOJSJD-UHFFFAOYSA-N 0.000 description 47
• 239000002244 precipitate Substances 0.000 description 47
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
• 235000019441 ethanol Nutrition 0.000 description 45
• 238000010992 reflux Methods 0.000 description 45
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 41
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
• 238000001953 recrystallisation Methods 0.000 description 35
• 229910052938 sodium sulfate Inorganic materials 0.000 description 35
• 235000011152 sodium sulphate Nutrition 0.000 description 35
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 33
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 32
• 235000019341 magnesium sulphate Nutrition 0.000 description 32
• 239000003208 petroleum Substances 0.000 description 32
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 31
• 230000005587 bubbling Effects 0.000 description 30
• 229910052799 carbon Inorganic materials 0.000 description 28
• 238000001816 cooling Methods 0.000 description 28
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 28
• 239000000047 product Substances 0.000 description 28
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 25
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 24
• 238000009835 boiling Methods 0.000 description 24
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
• 239000013078 crystal Substances 0.000 description 22
• 235000015497 potassium bicarbonate Nutrition 0.000 description 22
• 229910000028 potassium bicarbonate Inorganic materials 0.000 description 22
• 239000011736 potassium bicarbonate Substances 0.000 description 22
• JWMHRAUUHFSEJO-UHFFFAOYSA-N ethyl 2-[(3-nitropyridin-2-yl)amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1[N+]([O-])=O JWMHRAUUHFSEJO-UHFFFAOYSA-N 0.000 description 20
• 238000000354 decomposition reaction Methods 0.000 description 19
• 239000012458 free base Substances 0.000 description 18
• 239000011521 glass Substances 0.000 description 17
• 238000002360 preparation method Methods 0.000 description 17
• 238000003756 stirring Methods 0.000 description 17
• SHUQVZDDZJLFLH-UHFFFAOYSA-N 2-[2-(3-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetic acid Chemical compound N=1C2=CC=CN=C2N(CC(=O)O)C=1C1=CC=CC(Cl)=C1 SHUQVZDDZJLFLH-UHFFFAOYSA-N 0.000 description 16
• 238000002425 crystallisation Methods 0.000 description 15
• 239000000741 silica gel Substances 0.000 description 15
• 229910002027 silica gel Inorganic materials 0.000 description 15
• FAIHEMXOCGAZCC-UHFFFAOYSA-N 2-[2-(4-bromophenyl)imidazo[4,5-b]pyridin-3-yl]acetic acid Chemical compound N=1C2=CC=CN=C2N(CC(=O)O)C=1C1=CC=C(Br)C=C1 FAIHEMXOCGAZCC-UHFFFAOYSA-N 0.000 description 14
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
• 230000008025 crystallization Effects 0.000 description 14
• 229960004132 diethyl ether Drugs 0.000 description 13
• 239000005457 ice water Substances 0.000 description 13
• 239000008188 pellet Substances 0.000 description 13
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
• 239000000284 extract Substances 0.000 description 12
• 239000012044 organic layer Substances 0.000 description 12
• 229910000634 wood's metal Inorganic materials 0.000 description 12
• 229960000583 acetic acid Drugs 0.000 description 11
• 238000001035 drying Methods 0.000 description 11
• 238000001556 precipitation Methods 0.000 description 11
• UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 description 10
• RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 10
• FEOHNMCVUVSHJA-UHFFFAOYSA-N ethyl 2-[(3-aminopyridin-2-yl)amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1N FEOHNMCVUVSHJA-UHFFFAOYSA-N 0.000 description 10
• XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 10
• FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 10
• JPPWUNIENICFBZ-UHFFFAOYSA-N 2-[2-[4-(trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-3-yl]acetic acid Chemical compound N=1C2=CC=CN=C2N(CC(=O)O)C=1C1=CC=C(C(F)(F)F)C=C1 JPPWUNIENICFBZ-UHFFFAOYSA-N 0.000 description 9
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 238000001704 evaporation Methods 0.000 description 9
• 230000008020 evaporation Effects 0.000 description 9
• 238000007363 ring formation reaction Methods 0.000 description 9
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 8
• CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 8
• WGNUNYPERJMVRM-UHFFFAOYSA-N 3-pyridylacetic acid Chemical compound OC(=O)CC1=CC=CN=C1 WGNUNYPERJMVRM-UHFFFAOYSA-N 0.000 description 8
• 239000000463 material Substances 0.000 description 8
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 7
• 239000012267 brine Substances 0.000 description 7
• 239000012362 glacial acetic acid Substances 0.000 description 7
• 150000003254 radicals Chemical class 0.000 description 7
• 230000009467 reduction Effects 0.000 description 7
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
• 238000005303 weighing Methods 0.000 description 7
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 6
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• 150000001263 acyl chlorides Chemical class 0.000 description 6
• 239000002178 crystalline material Substances 0.000 description 6
• 229910001873 dinitrogen Inorganic materials 0.000 description 6
• WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
• GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 6
• DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 6
• SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
• WDPISXCGMFKLML-UHFFFAOYSA-N 2-(2-pyridin-2-ylimidazo[4,5-b]pyridin-3-yl)acetic acid Chemical compound N=1C2=CC=CN=C2N(CC(=O)O)C=1C1=CC=CC=N1 WDPISXCGMFKLML-UHFFFAOYSA-N 0.000 description 5
• JMTTXBKHYYLZOM-UHFFFAOYSA-N 2-[(3-nitropyridin-2-yl)amino]acetamide Chemical compound NC(=O)CNC1=NC=CC=C1[N+]([O-])=O JMTTXBKHYYLZOM-UHFFFAOYSA-N 0.000 description 5
• OXOWIQTYRUEQPJ-UHFFFAOYSA-N 2-[2-(3-bromophenyl)imidazo[4,5-b]pyridin-3-yl]acetic acid Chemical compound N=1C2=CC=CN=C2N(CC(=O)O)C=1C1=CC=CC(Br)=C1 OXOWIQTYRUEQPJ-UHFFFAOYSA-N 0.000 description 5
• SFFQMYWMUBFXKK-UHFFFAOYSA-N 2-[2-(4-methoxyphenyl)imidazo[4,5-b]pyridin-3-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC=CN=C2N1CC(O)=O SFFQMYWMUBFXKK-UHFFFAOYSA-N 0.000 description 5
• OXOUQFGMKIMPKX-UHFFFAOYSA-N 3-[2-(4-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]propanoic acid Chemical compound N=1C2=CC=CN=C2N(CCC(=O)O)C=1C1=CC=C(Cl)C=C1 OXOUQFGMKIMPKX-UHFFFAOYSA-N 0.000 description 5
• AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 5
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
• 230000015572 biosynthetic process Effects 0.000 description 5
• 239000003153 chemical reaction reagent Substances 0.000 description 5
• 239000000460 chlorine Substances 0.000 description 5
• 238000010828 elution Methods 0.000 description 5
• OYJXTOVLKZDGFK-UHFFFAOYSA-N ethanol;2-propan-2-yloxypropane Chemical compound CCO.CC(C)OC(C)C OYJXTOVLKZDGFK-UHFFFAOYSA-N 0.000 description 5
• IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 5
• 230000003311 flocculating effect Effects 0.000 description 5
• 238000006467 substitution reaction Methods 0.000 description 5
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 5
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
• 238000005406 washing Methods 0.000 description 5
• LSFZJGQFSJEDGF-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetic acid Chemical compound N=1C2=CC=CN=C2N(CC(=O)O)C=1C1=CC=C(Cl)C(Cl)=C1 LSFZJGQFSJEDGF-UHFFFAOYSA-N 0.000 description 4
• LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 4
• GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical class C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 4
• 239000007864 aqueous solution Substances 0.000 description 4
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• QXPDZDILEVKSOS-UHFFFAOYSA-N ethyl 2-[(6-chloro-3-nitropyridin-2-yl)amino]acetate Chemical compound CCOC(=O)CNC1=NC(Cl)=CC=C1[N+]([O-])=O QXPDZDILEVKSOS-UHFFFAOYSA-N 0.000 description 2
• YMUKCHUOTZASKI-UHFFFAOYSA-N ethyl 2-[(6-methoxy-3-nitropyridin-2-yl)amino]acetate Chemical compound CCOC(=O)CNC1=NC(OC)=CC=C1[N+]([O-])=O YMUKCHUOTZASKI-UHFFFAOYSA-N 0.000 description 2
• DIMFMYKPOPSSFY-UHFFFAOYSA-N ethyl 2-[(6-methyl-3-nitropyridin-2-yl)amino]acetate Chemical compound CCOC(=O)CNC1=NC(C)=CC=C1[N+]([O-])=O DIMFMYKPOPSSFY-UHFFFAOYSA-N 0.000 description 2
• ZUUUKTOPYGXELE-UHFFFAOYSA-N ethyl 2-[2-(2-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetate Chemical compound N=1C2=CC=CN=C2N(CC(=O)OCC)C=1C1=CC=CC=C1Cl ZUUUKTOPYGXELE-UHFFFAOYSA-N 0.000 description 2
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• NCRHULYHNNTUNM-UHFFFAOYSA-N ethyl 2-[2-(3-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetate Chemical compound N=1C2=CC=CN=C2N(CC(=O)OCC)C=1C1=CC=CC(Cl)=C1 NCRHULYHNNTUNM-UHFFFAOYSA-N 0.000 description 2
• OJZHDUHDBFUDBR-UHFFFAOYSA-N ethyl 2-[2-(4-bromophenyl)imidazo[4,5-b]pyridin-3-yl]acetate Chemical compound N=1C2=CC=CN=C2N(CC(=O)OCC)C=1C1=CC=C(Br)C=C1 OJZHDUHDBFUDBR-UHFFFAOYSA-N 0.000 description 2
• YDHLOYXHIPKIOF-UHFFFAOYSA-N ethyl 2-[2-(4-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetate Chemical compound N=1C2=CC=CN=C2N(CC(=O)OCC)C=1C1=CC=C(Cl)C=C1 YDHLOYXHIPKIOF-UHFFFAOYSA-N 0.000 description 2
• ANKPCGXGPYJRPP-UHFFFAOYSA-N ethyl 2-[2-(4-chloropyridin-2-yl)imidazo[4,5-b]pyridin-3-yl]acetate Chemical compound N=1C2=CC=CN=C2N(CC(=O)OCC)C=1C1=CC(Cl)=CC=N1 ANKPCGXGPYJRPP-UHFFFAOYSA-N 0.000 description 2
• FOLKHXDSCLCHKB-UHFFFAOYSA-N ethyl 2-[[2-(diethylamino)-6-methyl-3-nitropyridin-4-yl]amino]acetate Chemical compound CCOC(=O)CNC1=CC(C)=NC(N(CC)CC)=C1[N+]([O-])=O FOLKHXDSCLCHKB-UHFFFAOYSA-N 0.000 description 2
• QYTRJJOYBWKWDC-UHFFFAOYSA-N ethyl 2-[[2-[2-(3-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetyl]amino]acetate Chemical compound N=1C2=CC=CN=C2N(CC(=O)NCC(=O)OCC)C=1C1=CC=CC(Cl)=C1 QYTRJJOYBWKWDC-UHFFFAOYSA-N 0.000 description 2
• CBPLTBPMGINJCK-UHFFFAOYSA-N ethyl 2-[[3-(pyridine-2-carbonylamino)pyridin-2-yl]amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=CC=N1 CBPLTBPMGINJCK-UHFFFAOYSA-N 0.000 description 2
• PMFVRGZNHBYNHJ-UHFFFAOYSA-N ethyl 2-[[3-[(2-chlorobenzoyl)amino]pyridin-2-yl]amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=CC=C1Cl PMFVRGZNHBYNHJ-UHFFFAOYSA-N 0.000 description 2
• MFJQASCYUJILAX-UHFFFAOYSA-N ethyl 2-[[3-[(2-methoxybenzoyl)amino]pyridin-2-yl]amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=CC=C1OC MFJQASCYUJILAX-UHFFFAOYSA-N 0.000 description 2
• NOWNMJOJLPQMLB-UHFFFAOYSA-N ethyl 2-[[3-[(3-chlorobenzoyl)amino]pyridin-2-yl]amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=CC(Cl)=C1 NOWNMJOJLPQMLB-UHFFFAOYSA-N 0.000 description 2
• VYSOQIKAHVVYQB-UHFFFAOYSA-N ethyl 2-[[3-[(3-fluorobenzoyl)amino]pyridin-2-yl]amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=CC(F)=C1 VYSOQIKAHVVYQB-UHFFFAOYSA-N 0.000 description 2
• RHEZUULXGCTBLA-UHFFFAOYSA-N ethyl 2-[[3-[(4-bromobenzoyl)amino]pyridin-2-yl]amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=C(Br)C=C1 RHEZUULXGCTBLA-UHFFFAOYSA-N 0.000 description 2
• QWAIWRSSWLSZQY-UHFFFAOYSA-N ethyl 2-[[3-[(4-chlorobenzoyl)amino]pyridin-2-yl]amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=C(Cl)C=C1 QWAIWRSSWLSZQY-UHFFFAOYSA-N 0.000 description 2
• UXCMTYHWVLACKB-UHFFFAOYSA-N ethyl 2-[[3-[(4-methoxybenzoyl)amino]pyridin-2-yl]amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=C(OC)C=C1 UXCMTYHWVLACKB-UHFFFAOYSA-N 0.000 description 2
• FRPDDMHNNCIWIS-UHFFFAOYSA-N ethyl 2-[[3-[[3-(trifluoromethyl)benzoyl]amino]pyridin-2-yl]amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 FRPDDMHNNCIWIS-UHFFFAOYSA-N 0.000 description 2
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