NO803903L

NO803903L - Fremgangsmaate for fremstilling av antibakterielle cefalosporinderivater.

Fremgangsmaate for fremstilling av antibakterielle cefalosporinderivater.

Info

Publication number: NO803903L
Authority: NO; Norway
Prior art keywords: vol; radicals; product; carbon atoms; radical
Prior art date: 1979-12-24

Application number

NO803903A

Other languages

English (en)

Norwegian (no)

Inventor

Frederic Henri Jung

Original Assignee

Ici Pharma

Priority date

1979-12-24

Filing date

1980-12-22

Publication date

1981-06-25

1980-12-22 Application filed by Ici Pharma filed Critical Ici Pharma

1981-06-25 Publication of NO803903L publication Critical patent/NO803903L/no

Links

238000000034 method Methods 0.000 title claims description 108
238000002360 preparation method Methods 0.000 title claims description 20
230000000844 anti-bacterial effect Effects 0.000 title claims description 13
HOKIDJSKDBPKTQ-UHFFFAOYSA-N 3-(acetyloxymethyl)-7-[(5-amino-5-carboxypentanoyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C(NC(=O)CCCC(N)C(O)=O)C12 HOKIDJSKDBPKTQ-UHFFFAOYSA-N 0.000 title 1
-1 hydroxy, amino Chemical group 0.000 claims abstract description 605
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 44
229940124587 cephalosporin Drugs 0.000 claims abstract description 32
150000001780 cephalosporins Chemical class 0.000 claims abstract description 31
229930186147 Cephalosporin Natural products 0.000 claims abstract description 30
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 23
125000000217 alkyl group Chemical group 0.000 claims abstract description 19
239000001257 hydrogen Substances 0.000 claims abstract description 19
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
125000003118 aryl group Chemical group 0.000 claims abstract description 16
125000001424 substituent group Chemical group 0.000 claims abstract description 10
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 195
150000001875 compounds Chemical class 0.000 claims description 171
239000007858 starting material Substances 0.000 claims description 112
150000003254 radicals Chemical class 0.000 claims description 83
239000000460 chlorine Substances 0.000 claims description 62
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
230000008569 process Effects 0.000 claims description 28
150000003839 salts Chemical class 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 22
125000005843 halogen group Chemical group 0.000 claims description 19
239000012038 nucleophile Substances 0.000 claims description 18
229910052801 chlorine Inorganic materials 0.000 claims description 17
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
125000006239 protecting group Chemical group 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
239000012458 free base Substances 0.000 claims description 13
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
239000002585 base Substances 0.000 claims description 7
239000011593 sulfur Substances 0.000 claims description 7
230000002378 acidificating effect Effects 0.000 claims description 6
125000004103 aminoalkyl group Chemical group 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000001589 carboacyl group Chemical group 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
125000005236 alkanoylamino group Chemical group 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
150000001450 anions Chemical class 0.000 claims description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
UIBVOXFCGWJCTC-UHFFFAOYSA-N phenylmethylbenzene Chemical compound C=1C=CC=CC=1[CH]C1=CC=CC=C1 UIBVOXFCGWJCTC-UHFFFAOYSA-N 0.000 claims description 3
QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims description 2
125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 2
125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
238000007363 ring formation reaction Methods 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims 1
239000000463 material Substances 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
229910052736 halogen Inorganic materials 0.000 abstract 3
150000002367 halogens Chemical class 0.000 abstract 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract 2
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 2
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 1
125000003884 phenylalkyl group Chemical group 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 618
239000000047 product Substances 0.000 description 388
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 285
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 255
239000000243 solution Substances 0.000 description 204
238000006243 chemical reaction Methods 0.000 description 185
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 132
239000003480 eluent Substances 0.000 description 122
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 118
238000004587 chromatography analysis Methods 0.000 description 114
239000000741 silica gel Substances 0.000 description 107
229910002027 silica gel Inorganic materials 0.000 description 107
239000000203 mixture Substances 0.000 description 99
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 91
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 90
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 89
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 82
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 80
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 69
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 64
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 62
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 61
238000001556 precipitation Methods 0.000 description 52
229910004373 HOAc Inorganic materials 0.000 description 50
239000011541 reaction mixture Substances 0.000 description 50
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
239000002904 solvent Substances 0.000 description 47
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 45
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 43
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
238000001704 evaporation Methods 0.000 description 31
239000000725 suspension Substances 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
230000008020 evaporation Effects 0.000 description 28
235000019439 ethyl acetate Nutrition 0.000 description 27
VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 26
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 25
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 24
229910052757 nitrogen Inorganic materials 0.000 description 24
238000000354 decomposition reaction Methods 0.000 description 23
239000000706 filtrate Substances 0.000 description 23
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
229910052799 carbon Inorganic materials 0.000 description 19
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
238000000746 purification Methods 0.000 description 18
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 17
239000007787 solid Substances 0.000 description 17
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
239000002244 precipitate Substances 0.000 description 16
241000786363 Rhampholeon spectrum Species 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000003208 petroleum Substances 0.000 description 15
238000003756 stirring Methods 0.000 description 15
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
238000001914 filtration Methods 0.000 description 14
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
150000004985 diamines Chemical class 0.000 description 13
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 13
238000004090 dissolution Methods 0.000 description 13
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 12
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 12
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
229910052794 bromium Inorganic materials 0.000 description 11
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 10
238000001953 recrystallisation Methods 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
229910052786 argon Inorganic materials 0.000 description 9
239000000284 extract Substances 0.000 description 9
238000010438 heat treatment Methods 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 8
150000005840 aryl radicals Chemical class 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
238000009833 condensation Methods 0.000 description 8
230000005494 condensation Effects 0.000 description 8
238000001816 cooling Methods 0.000 description 8
239000003085 diluting agent Substances 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
125000000623 heterocyclic group Chemical group 0.000 description 8
238000004128 high performance liquid chromatography Methods 0.000 description 8
239000010410 layer Substances 0.000 description 8
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 7
229910052731 fluorine Inorganic materials 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
238000002953 preparative HPLC Methods 0.000 description 7
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
239000011737 fluorine Substances 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
125000004433 nitrogen atom Chemical group N* 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
238000001665 trituration Methods 0.000 description 6
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
LNFZAUNJFRYZLE-UHFFFAOYSA-N 2-fluoro-1h-imidazole Chemical compound FC1=NC=CN1 LNFZAUNJFRYZLE-UHFFFAOYSA-N 0.000 description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
125000004429 atom Chemical group 0.000 description 5
239000012267 brine Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
230000000694 effects Effects 0.000 description 5
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 5
239000000825 pharmaceutical preparation Substances 0.000 description 5
238000010898 silica gel chromatography Methods 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 5
239000005051 trimethylchlorosilane Substances 0.000 description 5
238000005406 washing Methods 0.000 description 5
VRHFDEUVCIAOLJ-UHFFFAOYSA-N 2-chloro-4,5-dihydro-1h-imidazole;hydrochloride Chemical compound Cl.ClC1=NCCN1 VRHFDEUVCIAOLJ-UHFFFAOYSA-N 0.000 description 4
GWSMACGSFHRVFA-UHFFFAOYSA-N 2-chloro-6-nitro-1h-benzimidazole Chemical compound [O-][N+](=O)C1=CC=C2N=C(Cl)NC2=C1 GWSMACGSFHRVFA-UHFFFAOYSA-N 0.000 description 4
RGHZNTJQDIXUPJ-UHFFFAOYSA-N 2-fluoro-1-tritylimidazole Chemical compound FC1=NC=CN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 RGHZNTJQDIXUPJ-UHFFFAOYSA-N 0.000 description 4
PGQMOPKRUZDRSC-UHFFFAOYSA-N 2-fluoro-1h-imidazole;hydrochloride Chemical compound Cl.FC1=NC=CN1 PGQMOPKRUZDRSC-UHFFFAOYSA-N 0.000 description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
230000031709 bromination Effects 0.000 description 4
238000005893 bromination reaction Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
125000001624 naphthyl group Chemical group 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
238000001228 spectrum Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
YYABOYVMXVMNPF-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;hydrobromide Chemical compound Br.OC(=O)C(F)(F)F YYABOYVMXVMNPF-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
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