NZ540147A - Oxazolidinone and/or isoxazoline derivatives as antibacterial agents - Google Patents

Info

Publication number

NZ540147A

NZ540147A NZ540147A NZ54014703A NZ540147A NZ 540147 A NZ540147 A NZ 540147A NZ 540147 A NZ540147 A NZ 540147A NZ 54014703 A NZ54014703 A NZ 54014703A NZ 540147 A NZ540147 A NZ 540147A

Authority

NZ

New Zealand

Prior art keywords

alkyl

ring

alkoxy

group

optionally substituted

Prior art date

2002-11-28

Links

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• Global Dossier
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• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title claims abstract description 41
• 239000003242 anti bacterial agent Substances 0.000 title claims abstract description 15
• 150000002547 isoxazolines Chemical class 0.000 title description 12
• 150000001875 compounds Chemical class 0.000 claims abstract description 256
• 150000002148 esters Chemical class 0.000 claims abstract description 148
• 239000000203 mixture Substances 0.000 claims abstract description 138
• 150000003839 salts Chemical class 0.000 claims abstract description 131
• 238000001727 in vivo Methods 0.000 claims abstract description 125
• 238000000034 method Methods 0.000 claims abstract description 60
• 125000003971 isoxazolinyl group Chemical class 0.000 claims abstract description 34
• 125000000217 alkyl group Chemical group 0.000 claims description 419
• -1 (l-4C)a]kylthio Chemical group 0.000 claims description 301
• 125000001424 substituent group Chemical group 0.000 claims description 147
• 239000007787 solid Substances 0.000 claims description 112
• 125000003545 alkoxy group Chemical group 0.000 claims description 110
• 229910052739 hydrogen Inorganic materials 0.000 claims description 89
• 229910052757 nitrogen Inorganic materials 0.000 claims description 78
• 229910052731 fluorine Inorganic materials 0.000 claims description 67
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
• 238000006243 chemical reaction Methods 0.000 claims description 61
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 57
• 239000001257 hydrogen Substances 0.000 claims description 57
• 229910052799 carbon Inorganic materials 0.000 claims description 53
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 47
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 46
• 125000005843 halogen group Chemical group 0.000 claims description 43
• 150000001721 carbon Chemical group 0.000 claims description 39
• 229910052717 sulfur Inorganic materials 0.000 claims description 36
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 35
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
• 125000002252 acyl group Chemical group 0.000 claims description 30
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 30
• 229910052760 oxygen Inorganic materials 0.000 claims description 30
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 29
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
• 125000005842 heteroatom Chemical group 0.000 claims description 28
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 26
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 26
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 25
• 125000004432 carbon atom Chemical group C* 0.000 claims description 25
• 125000003282 alkyl amino group Chemical group 0.000 claims description 24
• 230000008569 process Effects 0.000 claims description 24
• 238000005160 1H NMR spectroscopy Methods 0.000 claims description 23
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 23
• 150000002431 hydrogen Chemical class 0.000 claims description 21
• 125000000304 alkynyl group Chemical group 0.000 claims description 20
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 20
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 20
• 239000000651 prodrug Substances 0.000 claims description 20
• 229940002612 prodrug Drugs 0.000 claims description 20
• 125000003342 alkenyl group Chemical group 0.000 claims description 19
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 150000002367 halogens Chemical class 0.000 claims description 19
• 125000006239 protecting group Chemical group 0.000 claims description 19
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 18
• 125000004414 alkyl thio group Chemical group 0.000 claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims description 16
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 16
• 125000003118 aryl group Chemical group 0.000 claims description 15
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 15
• 125000002534 ethynyl group Chemical class [H]C#C* 0.000 claims description 15
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 15
• 230000000844 anti-bacterial effect Effects 0.000 claims description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
• 238000005859 coupling reaction Methods 0.000 claims description 13
• 125000001072 heteroaryl group Chemical group 0.000 claims description 13
• 125000004043 oxo group Chemical group O=* 0.000 claims description 13
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 12
• 125000000623 heterocyclic group Chemical group 0.000 claims description 12
• 230000008878 coupling Effects 0.000 claims description 11
• 238000010168 coupling process Methods 0.000 claims description 11
• 125000001153 fluoro group Chemical group F* 0.000 claims description 11
• 125000000464 thioxo group Chemical group S=* 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 10
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 10
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 9
• 229920006395 saturated elastomer Polymers 0.000 claims description 9
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 8
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 8
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
• 125000001589 carboacyl group Chemical group 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 150000002825 nitriles Chemical class 0.000 claims description 8
• 241001465754 Metazoa Species 0.000 claims description 7
• 150000001408 amides Chemical class 0.000 claims description 7
• 125000005418 aryl aryl group Chemical group 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000002619 bicyclic group Chemical group 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 7
• 125000004193 piperazinyl group Chemical group 0.000 claims description 7
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 7
• 241000894006 Bacteria Species 0.000 claims description 6
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
• 150000001540 azides Chemical class 0.000 claims description 6
• 125000001475 halogen functional group Chemical group 0.000 claims description 6
• 238000006467 substitution reaction Methods 0.000 claims description 6
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
• 125000004423 acyloxy group Chemical group 0.000 claims description 5
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
• 150000001412 amines Chemical class 0.000 claims description 5
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 5
• 238000002844 melting Methods 0.000 claims description 5
• 230000008018 melting Effects 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 229910052763 palladium Inorganic materials 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
• 229910052723 transition metal Inorganic materials 0.000 claims description 5
• 150000003624 transition metals Chemical class 0.000 claims description 5
• 150000003852 triazoles Chemical class 0.000 claims description 5
• 150000000177 1,2,3-triazoles Chemical class 0.000 claims description 4
• DVSMAFFYUWLENL-UHFFFAOYSA-N 3-(azidomethyl)-1,3-oxazolidin-2-one Chemical class [N-]=[N+]=NCN1CCOC1=O DVSMAFFYUWLENL-UHFFFAOYSA-N 0.000 claims description 4
• WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 4
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
• 150000001204 N-oxides Chemical class 0.000 claims description 4
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 239000003153 chemical reaction reagent Substances 0.000 claims description 4
• 230000000295 complement effect Effects 0.000 claims description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 4
• 230000003647 oxidation Effects 0.000 claims description 4
• 238000007254 oxidation reaction Methods 0.000 claims description 4
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 4
• 229910052700 potassium Inorganic materials 0.000 claims description 4
• 102220024746 rs199473444 Human genes 0.000 claims description 4
• 229940088594 vitamin Drugs 0.000 claims description 4
• 229930003231 vitamin Natural products 0.000 claims description 4
• 235000013343 vitamin Nutrition 0.000 claims description 4
• 239000011782 vitamin Substances 0.000 claims description 4
• 150000003722 vitamin derivatives Chemical class 0.000 claims description 4
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 3
• 241000192125 Firmicutes Species 0.000 claims description 3
• 125000006323 alkenyl amino group Chemical group 0.000 claims description 3
• 238000006352 cycloaddition reaction Methods 0.000 claims description 3
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 3
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 3
• 239000003701 inert diluent Substances 0.000 claims description 3
• 150000002923 oximes Chemical class 0.000 claims description 3
• 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 3
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 229930192474 thiophene Natural products 0.000 claims description 3
• NVZIFMAZKAYQJR-UHFFFAOYSA-N 3-(aminomethyl)-1,3-oxazolidin-2-one Chemical class NCN1CCOC1=O NVZIFMAZKAYQJR-UHFFFAOYSA-N 0.000 claims description 2
• VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims description 2
• 125000000676 alkoxyimino group Chemical group 0.000 claims description 2
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
• 125000005841 biaryl group Chemical group 0.000 claims description 2
• 238000006555 catalytic reaction Methods 0.000 claims description 2
• 150000001805 chlorine compounds Chemical class 0.000 claims description 2
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
• 239000012948 isocyanate Substances 0.000 claims description 2
• 150000002513 isocyanates Chemical class 0.000 claims description 2
• 125000002950 monocyclic group Chemical group 0.000 claims description 2
• 125000001624 naphthyl group Chemical group 0.000 claims description 2
• 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 2
• 150000002924 oxiranes Chemical class 0.000 claims description 2
• ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 2
• ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical compound OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 claims description 2
• 238000005956 quaternization reaction Methods 0.000 claims description 2
• 239000012048 reactive intermediate Substances 0.000 claims description 2
• 125000003003 spiro group Chemical group 0.000 claims description 2
• 239000000758 substrate Substances 0.000 claims description 2
• 150000003573 thiols Chemical class 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
• 150000001345 alkine derivatives Chemical group 0.000 claims 1
• 229940096118 ella Drugs 0.000 claims 1
• OOLLAFOLCSJHRE-ZHAKMVSLSA-N ulipristal acetate Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(OC(C)=O)C(C)=O)[C@]2(C)C1 OOLLAFOLCSJHRE-ZHAKMVSLSA-N 0.000 claims 1
• 230000000694 effects Effects 0.000 abstract description 16
• 244000000059 gram-positive pathogen Species 0.000 abstract description 8
• 230000003115 biocidal effect Effects 0.000 abstract description 7
• 206010041925 Staphylococcal infections Diseases 0.000 abstract 1
• 208000015688 methicillin-resistant staphylococcus aureus infectious disease Diseases 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 378
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 273
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 189
• 235000019439 ethyl acetate Nutrition 0.000 description 128
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 127
• 229940093499 ethyl acetate Drugs 0.000 description 122
• 229910001868 water Inorganic materials 0.000 description 118
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 109
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 106
• 239000000243 solution Substances 0.000 description 99
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 78
• 238000005481 NMR spectroscopy Methods 0.000 description 76
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 67
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
• 239000000047 product Substances 0.000 description 59
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 58
• 239000000741 silica gel Substances 0.000 description 58
• 229910002027 silica gel Inorganic materials 0.000 description 58
• 229960001866 silicon dioxide Drugs 0.000 description 58
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 52
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 41
• 239000000543 intermediate Substances 0.000 description 40
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 39
• 239000003921 oil Substances 0.000 description 35
• 235000019198 oils Nutrition 0.000 description 35
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 34
• 239000011737 fluorine Substances 0.000 description 34
• 229910052938 sodium sulfate Inorganic materials 0.000 description 34
• 235000011152 sodium sulphate Nutrition 0.000 description 34
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 30
• 239000011541 reaction mixture Substances 0.000 description 30
• 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 26
• 229910000027 potassium carbonate Inorganic materials 0.000 description 26
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 25
• 238000003756 stirring Methods 0.000 description 25
• 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 24
• 235000011181 potassium carbonates Nutrition 0.000 description 24
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
• 238000004440 column chromatography Methods 0.000 description 22
• 238000003818 flash chromatography Methods 0.000 description 22
• 239000012074 organic phase Substances 0.000 description 22
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
• 239000012044 organic layer Substances 0.000 description 20
• 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 20
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 19
• 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 17
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 17
• 238000004587 chromatography analysis Methods 0.000 description 17
• 125000001786 isothiazolyl group Chemical group 0.000 description 17
• 125000000842 isoxazolyl group Chemical group 0.000 description 17
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
• 235000019341 magnesium sulphate Nutrition 0.000 description 17
• 238000000746 purification Methods 0.000 description 17
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 16
• 239000002904 solvent Substances 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 15
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 15
• 238000001704 evaporation Methods 0.000 description 15
• 230000008020 evaporation Effects 0.000 description 15
• 239000000706 filtrate Substances 0.000 description 15
• 239000000725 suspension Substances 0.000 description 15
• BORXYEDGSCEATN-UHFFFAOYSA-N 3-(triazol-1-ylmethyl)-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1CN1N=NC=C1 BORXYEDGSCEATN-UHFFFAOYSA-N 0.000 description 14
• 239000012267 brine Substances 0.000 description 14
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 14
• 238000010828 elution Methods 0.000 description 14
• 239000002244 precipitate Substances 0.000 description 14
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
• 239000012043 crude product Substances 0.000 description 13
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 13
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
• 239000000463 material Substances 0.000 description 12
• 239000000843 powder Substances 0.000 description 12
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
• 239000002253 acid Substances 0.000 description 11
• 125000005997 bromomethyl group Chemical group 0.000 description 11
• 125000001309 chloro group Chemical group Cl* 0.000 description 11
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