KR20100105847A - 항균성 농축 티아졸 - Google Patents

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Publication number

KR20100105847A

KR20100105847A KR20107015443A KR20107015443A KR20100105847A KR 20100105847 A KR20100105847 A KR 20100105847A KR 20107015443 A KR20107015443 A KR 20107015443A KR 20107015443 A KR20107015443 A KR 20107015443A KR 20100105847 A KR20100105847 A KR 20100105847A

Authority

KR

South Korea

Prior art keywords

mmol

reaction mixture

minutes

optionally substituted

added

Prior art date

2007-12-13

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Ceased

Links

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• Global Dossier
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• 230000000844 anti-bacterial effect Effects 0.000 title abstract description 4
• 150000003557 thiazoles Chemical class 0.000 title 1
• -1 methoxy, mercapto, mercaptomethyl Chemical group 0.000 claims abstract description 168
• 150000001875 compounds Chemical class 0.000 claims abstract description 90
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
• 239000001257 hydrogen Substances 0.000 claims abstract description 26
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 23
• 125000006413 ring segment Chemical group 0.000 claims abstract description 20
• 125000001424 substituent group Chemical group 0.000 claims abstract description 20
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 11
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
• 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
• 150000003568 thioethers Chemical class 0.000 claims abstract description 7
• 125000004419 alkynylene group Chemical group 0.000 claims abstract description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 6
• 150000002825 nitriles Chemical class 0.000 claims abstract description 6
• 125000004450 alkenylene group Chemical group 0.000 claims abstract description 5
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 5
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 5
• 125000001620 monocyclic carbocycle group Chemical group 0.000 claims abstract description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 5
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims abstract description 4
• 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims abstract description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 4
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
• 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims abstract description 4
• 229910052799 carbon Chemical group 0.000 claims abstract description 4
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract 4
• 125000001475 halogen functional group Chemical group 0.000 claims abstract 2
• 238000002360 preparation method Methods 0.000 claims description 67
• 239000000203 mixture Substances 0.000 claims description 32
• 238000000034 method Methods 0.000 claims description 31
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 26
• 230000001580 bacterial effect Effects 0.000 claims description 22
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 17
• 230000000845 anti-microbial effect Effects 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 12
• 150000002431 hydrogen Chemical class 0.000 claims description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• 208000035143 Bacterial infection Diseases 0.000 claims description 7
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 7
• 125000003386 piperidinyl group Chemical group 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
• 238000011109 contamination Methods 0.000 claims description 5
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims description 3
• 150000001204 N-oxides Chemical class 0.000 claims description 3
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 239000000758 substrate Substances 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 239000004599 antimicrobial Substances 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims 1
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 384
• 239000011541 reaction mixture Substances 0.000 description 381
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 333
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 251
• 229910052757 nitrogen Inorganic materials 0.000 description 195
• 239000000243 solution Substances 0.000 description 185
• 238000006243 chemical reaction Methods 0.000 description 171
• 238000012544 monitoring process Methods 0.000 description 161
• 238000004809 thin layer chromatography Methods 0.000 description 161
• YNHIGQDRGKUECZ-UHFFFAOYSA-L PdCl2(PPh3)2 Substances [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 145
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 131
• 239000000047 product Substances 0.000 description 128
• 235000019439 ethyl acetate Nutrition 0.000 description 117
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 112
• 239000011734 sodium Substances 0.000 description 112
• 238000005481 NMR spectroscopy Methods 0.000 description 101
• 239000012267 brine Substances 0.000 description 96
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 96
• 238000005406 washing Methods 0.000 description 86
• 239000000741 silica gel Substances 0.000 description 85
• 229910002027 silica gel Inorganic materials 0.000 description 85
• 229960001866 silicon dioxide Drugs 0.000 description 85
• WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 77
• 238000004128 high performance liquid chromatography Methods 0.000 description 74
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 74
• LMFDEUSLYJMRRF-UHFFFAOYSA-N (5-bromo-2,4-difluorophenyl)thiourea Chemical compound NC(=S)NC1=CC(Br)=C(F)C=C1F LMFDEUSLYJMRRF-UHFFFAOYSA-N 0.000 description 68
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 68
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 68
• 239000005457 ice water Substances 0.000 description 66
• 239000012043 crude product Substances 0.000 description 63
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 61
• PBHAKKGKJYGQLT-UHFFFAOYSA-N 1-ethyl-3-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1B1OC(C)(C)C(C)(C)O1 PBHAKKGKJYGQLT-UHFFFAOYSA-N 0.000 description 60
• 239000004202 carbamide Substances 0.000 description 60
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 56
• 238000004519 manufacturing process Methods 0.000 description 52
• 150000007942 carboxylates Chemical class 0.000 description 51
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 46
• IBDINBYDLQQKTJ-UHFFFAOYSA-N 1-(5-bromo-6-fluoro-1,3-benzothiazol-2-yl)-3-ethylurea Chemical compound BrC1=C(F)C=C2SC(NC(=O)NCC)=NC2=C1 IBDINBYDLQQKTJ-UHFFFAOYSA-N 0.000 description 43
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 37
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 35
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
• WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 34
• 239000000706 filtrate Substances 0.000 description 33
• 239000007787 solid Substances 0.000 description 33
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 33
• 238000000746 purification Methods 0.000 description 32
• 239000007983 Tris buffer Substances 0.000 description 26
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 23
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 18
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 18
• RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 16
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
• 101150003085 Pdcl gene Proteins 0.000 description 16
• NCCRJWXFDGJZLM-UHFFFAOYSA-N 1-(5-bromo-1,3-benzothiazol-2-yl)-3-ethylurea Chemical compound BrC1=CC=C2SC(NC(=O)NCC)=NC2=C1 NCCRJWXFDGJZLM-UHFFFAOYSA-N 0.000 description 15
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
• 108090000769 Isomerases Proteins 0.000 description 15
• 102000004195 Isomerases Human genes 0.000 description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 230000000694 effects Effects 0.000 description 15
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
• 239000002904 solvent Substances 0.000 description 14
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 13
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
• WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 12
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
• OUGDMTDLPBUYFK-UHFFFAOYSA-N n-methyl-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide Chemical compound C1=NC(CC(=O)NC)=CC=C1B1OC(C)(C)C(C)(C)O1 OUGDMTDLPBUYFK-UHFFFAOYSA-N 0.000 description 11
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
• 235000008504 concentrate Nutrition 0.000 description 10
• 239000012141 concentrate Substances 0.000 description 10
• 239000012299 nitrogen atmosphere Substances 0.000 description 10
• 238000003756 stirring Methods 0.000 description 10
• 239000000725 suspension Substances 0.000 description 10
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
• SSLMGOKTIUIZLY-UHFFFAOYSA-N 4-bromo-1h-pyridin-2-one Chemical compound OC1=CC(Br)=CC=N1 SSLMGOKTIUIZLY-UHFFFAOYSA-N 0.000 description 9
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
• 229960000583 acetic acid Drugs 0.000 description 9
• 125000004432 carbon atom Chemical group C* 0.000 description 9
• 241000894006 Bacteria Species 0.000 description 8
• 239000000377 silicon dioxide Substances 0.000 description 8
• 235000011121 sodium hydroxide Nutrition 0.000 description 8
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 8
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 8
• DIOHEXPTUTVCNX-UHFFFAOYSA-N 1,1,1-trifluoro-n-phenyl-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)N(S(=O)(=O)C(F)(F)F)C1=CC=CC=C1 DIOHEXPTUTVCNX-UHFFFAOYSA-N 0.000 description 7
• HENXUFOAGXNWKH-UHFFFAOYSA-N 3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=CN=CC(B2OC(C)(C)C(C)(C)O2)=C1 HENXUFOAGXNWKH-UHFFFAOYSA-N 0.000 description 7
• 125000003118 aryl group Chemical group 0.000 description 7
• 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 7
• CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 7
• 230000015572 biosynthetic process Effects 0.000 description 7
• 239000003814 drug Substances 0.000 description 7
• 239000012044 organic layer Substances 0.000 description 7
• PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
• 235000011118 potassium hydroxide Nutrition 0.000 description 7
• ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 7
• 238000003786 synthesis reaction Methods 0.000 description 7
• 108020004414 DNA Proteins 0.000 description 6
• 102000004190 Enzymes Human genes 0.000 description 6
• 108090000790 Enzymes Proteins 0.000 description 6
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 125000001072 heteroaryl group Chemical group 0.000 description 6
• 125000000842 isoxazolyl group Chemical group 0.000 description 6
• 239000010410 layer Substances 0.000 description 6
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 6
• 239000002480 mineral oil Substances 0.000 description 6
• 235000010446 mineral oil Nutrition 0.000 description 6
• 125000002950 monocyclic group Chemical group 0.000 description 6
• NSYSSMYQPLSPOD-UHFFFAOYSA-N triacetate lactone Chemical compound CC1=CC(O)=CC(=O)O1 NSYSSMYQPLSPOD-UHFFFAOYSA-N 0.000 description 6
• 238000005160 1H NMR spectroscopy Methods 0.000 description 5
• IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 5
• LLFSFJYWGVKYRP-UHFFFAOYSA-N 4-bromo-6-methylpyran-2-one Chemical compound CC1=CC(Br)=CC(=O)O1 LLFSFJYWGVKYRP-UHFFFAOYSA-N 0.000 description 5
• BSDBYOISRBJVEO-UHFFFAOYSA-N 5-bromo-6-fluoro-1,3-benzothiazole Chemical compound BrC=1C(=CC2=C(N=CS2)C=1)F BSDBYOISRBJVEO-UHFFFAOYSA-N 0.000 description 5
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
• AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 5
• 239000003242 anti bacterial agent Substances 0.000 description 5
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 5
• 238000007664 blowing Methods 0.000 description 5
• 229910052796 boron Inorganic materials 0.000 description 5
• 235000019441 ethanol Nutrition 0.000 description 5
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
• 230000008570 general process Effects 0.000 description 5
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
• 235000011056 potassium acetate Nutrition 0.000 description 5
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 5
• NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 5
• 229920006395 saturated elastomer Polymers 0.000 description 5
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