TWI631119B - 抗菌雙芳香族衍生物 - Google Patents

Info

Publication number

TWI631119B

TWI631119B TW103113729A TW103113729A TWI631119B TW I631119 B TWI631119 B TW I631119B TW 103113729 A TW103113729 A TW 103113729A TW 103113729 A TW103113729 A TW 103113729A TW I631119 B TWI631119 B TW I631119B

Authority

TW

Taiwan

Prior art keywords

oxo

ethyl

pyrido

oxazin

methoxy

Prior art date

2013-04-16

Links

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• 230000000844 anti-bacterial effect Effects 0.000 title abstract description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 498
• -1 cyanomethoxy Chemical group 0.000 claims abstract description 330
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 153
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 64
• 150000003839 salts Chemical class 0.000 claims abstract description 64
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 35
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 29
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 25
• 150000002367 halogens Chemical class 0.000 claims abstract description 25
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 11
• 229910052770 Uranium Inorganic materials 0.000 claims description 105
• 238000004519 manufacturing process Methods 0.000 claims description 97
• 208000015181 infectious disease Diseases 0.000 claims description 38
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 34
• WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 31
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 29
• 208000035143 Bacterial infection Diseases 0.000 claims description 28
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 28
• 230000001404 mediated effect Effects 0.000 claims description 21
• 239000003814 drug Substances 0.000 claims description 20
• 241000191967 Staphylococcus aureus Species 0.000 claims description 18
• 229910052720 vanadium Inorganic materials 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 241000588626 Acinetobacter baumannii Species 0.000 claims description 10
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
• 206010033078 Otitis media Diseases 0.000 claims description 4
• 206010035664 Pneumonia Diseases 0.000 claims description 4
• 206010057190 Respiratory tract infections Diseases 0.000 claims description 4
• 206010062255 Soft tissue infection Diseases 0.000 claims description 4
• 229940079593 drug Drugs 0.000 claims description 4
• 206010040872 skin infection Diseases 0.000 claims description 4
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
• FBXGQDUVJBKEAJ-UHFFFAOYSA-N 4h-oxazin-3-one Chemical compound O=C1CC=CON1 FBXGQDUVJBKEAJ-UHFFFAOYSA-N 0.000 claims description 3
• 208000016604 Lyme disease Diseases 0.000 claims description 3
• 201000009906 Meningitis Diseases 0.000 claims description 3
• 206010031252 Osteomyelitis Diseases 0.000 claims description 3
• 206010014665 endocarditis Diseases 0.000 claims description 3
• JNRLAFVOGSWMDW-LBAQZLPGSA-N 6-[(5s)-5-[2-[[3-[6-(3-hydroxypyrrolidin-1-yl)pyridin-2-yl]phenyl]methylamino]ethyl]-2-oxo-1,3-oxazolidin-3-yl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound C1C(O)CCN1C1=CC=CC(C=2C=C(CNCC[C@@H]3OC(=O)N(C3)C=3N=C4NC(=O)COC4=CC=3)C=CC=2)=N1 JNRLAFVOGSWMDW-LBAQZLPGSA-N 0.000 claims description 2
• RQOXQPQDAZOHPM-UHFFFAOYSA-N 6-[5-[2-[[2-hydroxy-3-(6-methoxypyridin-2-yl)phenyl]methylamino]ethyl]-2-oxo-1,3-oxazol-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound OC1=C(CNCCC2=CN(C(O2)=O)C=2C=CC=3OCC(NC=3N=2)=O)C=CC=C1C1=NC(=CC=C1)OC RQOXQPQDAZOHPM-UHFFFAOYSA-N 0.000 claims description 2
• LRPWEWYMTXMULF-UHFFFAOYSA-N 6-[5-[2-[[3-(3-methoxyphenyl)phenyl]methylamino]ethyl]-2-oxo-1,3-oxazol-3-yl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound COC1=CC=CC(C=2C=C(CNCCC=3OC(=O)N(C=4N=C5NC(=O)COC5=CC=4)C=3)C=CC=2)=C1 LRPWEWYMTXMULF-UHFFFAOYSA-N 0.000 claims description 2
• 206010056519 Abdominal infection Diseases 0.000 claims description 2
• 208000031729 Bacteremia Diseases 0.000 claims description 2
• 208000037384 Clostridium Infections Diseases 0.000 claims description 2
• 206010017964 Gastrointestinal infection Diseases 0.000 claims description 2
• 239000004480 active ingredient Substances 0.000 claims description 2
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 208000037972 tropical disease Diseases 0.000 claims description 2
• 201000008827 tuberculosis Diseases 0.000 claims description 2
• 208000019206 urinary tract infection Diseases 0.000 claims description 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N 3-methoxypyridine Chemical compound COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
• NSGNREBTEFKPIL-UHFFFAOYSA-N 4-methoxypyridazine Chemical compound COC1=CC=NN=C1 NSGNREBTEFKPIL-UHFFFAOYSA-N 0.000 claims 1
• GTFMIJNXNMDHAB-UHFFFAOYSA-N 4h-1,4-benzothiazin-3-one Chemical compound C1=CC=C2NC(=O)CSC2=C1 GTFMIJNXNMDHAB-UHFFFAOYSA-N 0.000 claims 1
• QRCGFTXRXYMJOS-UHFFFAOYSA-N 4h-1,4-benzoxazin-3-one Chemical compound C1=CC=C2NC(=O)COC2=C1 QRCGFTXRXYMJOS-UHFFFAOYSA-N 0.000 claims 1
• UJWGONOAEPXGBS-QGZVFWFLSA-N 6-[(5r)-5-[2-[[3-(5-methoxypyridazin-3-yl)phenyl]methylamino]ethyl]-2-oxo-1,3-oxazolidin-3-yl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound COC1=CN=NC(C=2C=C(CNCC[C@H]3OC(=O)N(C3)C=3N=C4NC(=O)COC4=CC=3)C=CC=2)=C1 UJWGONOAEPXGBS-QGZVFWFLSA-N 0.000 claims 1
• IRANJLSGXRDNGR-IBGZPJMESA-N 6-[(5s)-5-[2-[[3-(2-methoxypyridin-4-yl)phenyl]methylamino]ethyl]-2-oxo-1,3-oxazolidin-3-yl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound C1=NC(OC)=CC(C=2C=C(CNCC[C@@H]3OC(=O)N(C3)C=3N=C4NC(=O)COC4=CC=3)C=CC=2)=C1 IRANJLSGXRDNGR-IBGZPJMESA-N 0.000 claims 1
• YPANFOWCQUODJD-QFIPXVFZSA-N 6-[(5s)-5-[2-[[3-(3-ethoxyphenyl)phenyl]methylamino]ethyl]-2-oxo-1,3-oxazolidin-3-yl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound CCOC1=CC=CC(C=2C=C(CNCC[C@@H]3OC(=O)N(C3)C=3N=C4NC(=O)COC4=CC=3)C=CC=2)=C1 YPANFOWCQUODJD-QFIPXVFZSA-N 0.000 claims 1
• SMKHTJKJAPOWDC-IBGZPJMESA-N 6-[2-hydroxy-3-[[2-[(5S)-2-oxo-3-(3-oxo-4H-1,4-benzoxazin-6-yl)-1,3-oxazolidin-5-yl]ethylamino]methyl]phenyl]pyridine-2-carbonitrile Chemical compound OC1=C(C=CC=C1CNCC[C@H]1CN(C(O1)=O)C=1C=CC2=C(NC(CO2)=O)C=1)C1=CC=CC(=N1)C#N SMKHTJKJAPOWDC-IBGZPJMESA-N 0.000 claims 1
• CDDXGMSKEASLEP-UHFFFAOYSA-N 6-[2-hydroxy-3-[[2-[2-oxo-3-(3-oxo-4H-pyrido[3,2-b][1,4]oxazin-6-yl)-1,3-oxazol-5-yl]ethylamino]methyl]phenyl]pyridine-2-carbonitrile Chemical compound OC1=C(C=CC=C1CNCCC1=CN(C(O1)=O)C=1C=CC=2OCC(NC=2N=1)=O)C1=CC=CC(=N1)C#N CDDXGMSKEASLEP-UHFFFAOYSA-N 0.000 claims 1
• HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims 1
• LAADXKOYLRGLQX-UHFFFAOYSA-N C1CC1COC2=CC=CC(=C2)C3=CC=CC=C3 Chemical group C1CC1COC2=CC=CC(=C2)C3=CC=CC=C3 LAADXKOYLRGLQX-UHFFFAOYSA-N 0.000 claims 1
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 1
• 239000004305 biphenyl Substances 0.000 claims 1
• 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract description 4
• 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract description 3
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 abstract description 3
• PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 abstract description 2
• 238000000034 method Methods 0.000 description 251
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 132
• 238000000746 purification Methods 0.000 description 130
• 238000002953 preparative HPLC Methods 0.000 description 112
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
• 239000007787 solid Substances 0.000 description 95
• 239000002253 acid Substances 0.000 description 79
• 239000000203 mixture Substances 0.000 description 75
• 238000002360 preparation method Methods 0.000 description 74
• 239000000543 intermediate Substances 0.000 description 67
• 230000002829 reductive effect Effects 0.000 description 62
• 238000005481 NMR spectroscopy Methods 0.000 description 60
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
• 239000000843 powder Substances 0.000 description 53
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 52
• 238000006243 chemical reaction Methods 0.000 description 49
• 239000006260 foam Substances 0.000 description 45
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 41
• 239000011541 reaction mixture Substances 0.000 description 41
• 239000000243 solution Substances 0.000 description 40
• 239000000725 suspension Substances 0.000 description 39
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 38
• 125000004432 carbon atom Chemical group C* 0.000 description 36
• 239000012044 organic layer Substances 0.000 description 33
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• 239000010410 layer Substances 0.000 description 26
• 239000003921 oil Substances 0.000 description 25
• 235000019198 oils Nutrition 0.000 description 25
• 239000000706 filtrate Substances 0.000 description 24
• 238000001914 filtration Methods 0.000 description 24
• UFTCBKDCPYVACN-SECBINFHSA-N (5r)-5-(2-aminoethyl)-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](CCN)CN1C1=CC=C(SCC(=O)N2)C2=C1 UFTCBKDCPYVACN-SECBINFHSA-N 0.000 description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• 239000003480 eluent Substances 0.000 description 19
• 239000012267 brine Substances 0.000 description 18
• 229920006395 saturated elastomer Polymers 0.000 description 18
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
• HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 16
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 16
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
• 229910052799 carbon Inorganic materials 0.000 description 15
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 14
• 241000894006 Bacteria Species 0.000 description 14
• 239000003054 catalyst Substances 0.000 description 14
• 229910052739 hydrogen Inorganic materials 0.000 description 14
• 229910052763 palladium Inorganic materials 0.000 description 14
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 13
• 239000002904 solvent Substances 0.000 description 13
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
• 239000000460 chlorine Substances 0.000 description 12
• 229910052740 iodine Inorganic materials 0.000 description 12
• 239000001257 hydrogen Substances 0.000 description 11
• 125000006239 protecting group Chemical group 0.000 description 11
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 10
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
• 239000012043 crude product Substances 0.000 description 10
• 238000000105 evaporative light scattering detection Methods 0.000 description 10
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
• 150000002148 esters Chemical class 0.000 description 9
• 238000004128 high performance liquid chromatography Methods 0.000 description 9
• 238000001665 trituration Methods 0.000 description 9
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
• PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
• 230000002265 prevention Effects 0.000 description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
• 241000589517 Pseudomonas aeruginosa Species 0.000 description 7
• 125000000217 alkyl group Chemical group 0.000 description 7
• 230000015572 biosynthetic process Effects 0.000 description 7
• 125000000753 cycloalkyl group Chemical group 0.000 description 7
• 238000001514 detection method Methods 0.000 description 7
• DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 7
• 229910052731 fluorine Inorganic materials 0.000 description 7
• 239000011737 fluorine Substances 0.000 description 7
• 239000003365 glass fiber Substances 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• XLGRINRFBNCHQS-UHFFFAOYSA-N 3-chloro-5-methoxypyridazine Chemical compound COC1=CN=NC(Cl)=C1 XLGRINRFBNCHQS-UHFFFAOYSA-N 0.000 description 6
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
• 241000192125 Firmicutes Species 0.000 description 6
• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• 150000001412 amines Chemical class 0.000 description 6
• 239000003242 anti bacterial agent Substances 0.000 description 6
• 239000007864 aqueous solution Substances 0.000 description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
• 229910052794 bromium Inorganic materials 0.000 description 6
• 239000003795 chemical substances by application Substances 0.000 description 6
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• 239000012230 colorless oil Substances 0.000 description 6
• 235000019253 formic acid Nutrition 0.000 description 6
• 230000002401 inhibitory effect Effects 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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• 238000003786 synthesis reaction Methods 0.000 description 6
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• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
• SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 description 5
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
• 241000606768 Haemophilus influenzae Species 0.000 description 5
• 241000193998 Streptococcus pneumoniae Species 0.000 description 5
• 241000193996 Streptococcus pyogenes Species 0.000 description 5
• 239000008346 aqueous phase Substances 0.000 description 5
• 229910052786 argon Inorganic materials 0.000 description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
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• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
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• 238000010561 standard procedure Methods 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• 229940031000 streptococcus pneumoniae Drugs 0.000 description 5
• 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
• 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 4
• 238000005160 1H NMR spectroscopy Methods 0.000 description 4
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
• GLGWNAPAIMXRGT-UHFFFAOYSA-N 3-(3-methoxyphenyl)benzaldehyde Chemical compound COC1=CC=CC(C=2C=C(C=O)C=CC=2)=C1 GLGWNAPAIMXRGT-UHFFFAOYSA-N 0.000 description 4
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
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