NZ521117A - Method of treating or inhibiting colonic polyps - Google Patents

Info

Publication number

NZ521117A

NZ521117A NZ521117A NZ52111701A NZ521117A NZ 521117 A NZ521117 A NZ 521117A NZ 521117 A NZ521117 A NZ 521117A NZ 52111701 A NZ52111701 A NZ 52111701A NZ 521117 A NZ521117 A NZ 521117A

Authority

NZ

New Zealand

Prior art keywords

amino

carbonitrile

phenylamino

quinolinecarbonitrile

cyano

Prior art date

2000-03-13

Links

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• Global Dossier
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• 208000035984 Colonic Polyps Diseases 0.000 title claims abstract description 11
• 230000002401 inhibitory effect Effects 0.000 title claims abstract description 8
• 238000000034 method Methods 0.000 title description 40
• -1 cyanoquinoline compound Chemical class 0.000 claims abstract description 116
• 150000003839 salts Chemical class 0.000 claims abstract description 16
• 238000002360 preparation method Methods 0.000 claims abstract description 13
• 239000003814 drug Substances 0.000 claims abstract description 5
• 125000004432 carbon atom Chemical group C* 0.000 claims description 214
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 112
• 150000001875 compounds Chemical class 0.000 claims description 100
• 102100028701 General vesicular transport factor p115 Human genes 0.000 claims description 60
• 101000767151 Homo sapiens General vesicular transport factor p115 Proteins 0.000 claims description 60
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 43
• 125000000217 alkyl group Chemical group 0.000 claims description 43
• WDXARTMCIRVMAE-UHFFFAOYSA-N quinoline-2-carbonitrile Chemical compound C1=CC=CC2=NC(C#N)=CC=C21 WDXARTMCIRVMAE-UHFFFAOYSA-N 0.000 claims description 26
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
• 238000001953 recrystallisation Methods 0.000 claims description 19
• 239000001257 hydrogen Substances 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• ZRTXZWXHWPAXFT-UHFFFAOYSA-N 6-amino-4-(3-bromoanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 ZRTXZWXHWPAXFT-UHFFFAOYSA-N 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• LUEHNHVFDCZTGL-UHFFFAOYSA-N but-2-ynoic acid Chemical compound CC#CC(O)=O LUEHNHVFDCZTGL-UHFFFAOYSA-N 0.000 claims description 13
• 238000004587 chromatography analysis Methods 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 125000005843 halogen group Chemical group 0.000 claims description 12
• 125000004970 halomethyl group Chemical group 0.000 claims description 11
• LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 10
• 125000004849 alkoxymethyl group Chemical group 0.000 claims description 10
• 125000000304 alkynyl group Chemical group 0.000 claims description 10
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• TYPPJPWWUXMGRI-UHFFFAOYSA-N 4-(diethylamino)but-2-enoic acid Chemical compound CCN(CC)CC=CC(O)=O TYPPJPWWUXMGRI-UHFFFAOYSA-N 0.000 claims description 9
• 125000004429 atom Chemical group 0.000 claims description 9
• QZZYYBQGTSGDPP-UHFFFAOYSA-N quinoline-3-carbonitrile Chemical compound C1=CC=CC2=CC(C#N)=CN=C21 QZZYYBQGTSGDPP-UHFFFAOYSA-N 0.000 claims description 9
• 125000005042 acyloxymethyl group Chemical group 0.000 claims description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• DOTGZROJTAUYFQ-OWOJBTEDSA-N (e)-4-bromobut-2-enoic acid Chemical compound OC(=O)\C=C\CBr DOTGZROJTAUYFQ-OWOJBTEDSA-N 0.000 claims description 7
• WMSREFWREGHLAP-UHFFFAOYSA-N 6-amino-4-(3-chloro-4-fluoroanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 WMSREFWREGHLAP-UHFFFAOYSA-N 0.000 claims description 7
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
• ITGIYLMMAABTHC-ONEGZZNKSA-N (e)-4-(dimethylazaniumyl)but-2-enoate Chemical compound CN(C)C\C=C\C(O)=O ITGIYLMMAABTHC-ONEGZZNKSA-N 0.000 claims description 6
• LQFDQJDIWFMWHN-UHFFFAOYSA-N 4-morpholin-4-ylbut-2-enoic acid Chemical compound OC(=O)C=CCN1CCOCC1 LQFDQJDIWFMWHN-UHFFFAOYSA-N 0.000 claims description 6
• IMBMTYREOJZAAW-UHFFFAOYSA-N 6-amino-4-(3-bromoanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(N)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 IMBMTYREOJZAAW-UHFFFAOYSA-N 0.000 claims description 6
• 125000003282 alkyl amino group Chemical group 0.000 claims description 6
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
• 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 6
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• UMAUXDSUHUAKMF-UHFFFAOYSA-N chembl111586 Chemical compound C=12C=C(O)C(O)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 UMAUXDSUHUAKMF-UHFFFAOYSA-N 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 6
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 6
• CLGJOTLYNXUVES-UHFFFAOYSA-N 6-amino-4-(3-bromo-4-fluoroanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Br)=C1 CLGJOTLYNXUVES-UHFFFAOYSA-N 0.000 claims description 5
• 241000124008 Mammalia Species 0.000 claims description 5
• 125000004423 acyloxy group Chemical group 0.000 claims description 5
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
• 125000001246 bromo group Chemical group Br* 0.000 claims description 5
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 5
• AJSYUAVIQGKJFW-UHFFFAOYSA-N 6-amino-4-(3,4-dibromoanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=C(Br)C(Br)=C1 AJSYUAVIQGKJFW-UHFFFAOYSA-N 0.000 claims description 4
• MJPIXAAXFZASFT-UHFFFAOYSA-N 6-amino-4-(3-ethynylanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#C)=C1 MJPIXAAXFZASFT-UHFFFAOYSA-N 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 125000000033 alkoxyamino group Chemical group 0.000 claims description 4
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• IYVDPTGYWDFGTF-SREVYHEPSA-N (z)-n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-3-chloroprop-2-enamide Chemical compound C12=CC(NC(=O)\C=C/Cl)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 IYVDPTGYWDFGTF-SREVYHEPSA-N 0.000 claims description 3
• RUGCZQOSGFAGFE-UHFFFAOYSA-N 4-(3,4-dibromoanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=C(Br)C(Br)=C1 RUGCZQOSGFAGFE-UHFFFAOYSA-N 0.000 claims description 3
• MZQKSJFIOAVZJR-UHFFFAOYSA-N 4-(3-aminoanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(N)=C1 MZQKSJFIOAVZJR-UHFFFAOYSA-N 0.000 claims description 3
• CQKFTSMPIIYOBX-UHFFFAOYSA-N 4-(3-bromoanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 CQKFTSMPIIYOBX-UHFFFAOYSA-N 0.000 claims description 3
• BISJVYCVPJVRKJ-UHFFFAOYSA-N 4-(3-bromoanilino)-7-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound C=12C=C([N+]([O-])=O)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 BISJVYCVPJVRKJ-UHFFFAOYSA-N 0.000 claims description 3
• NWVCFCJOJVDBHH-UHFFFAOYSA-N 4-(methylamino)but-2-enoic acid Chemical compound CNCC=CC(O)=O NWVCFCJOJVDBHH-UHFFFAOYSA-N 0.000 claims description 3
• MJOPKUFLFODTKP-UHFFFAOYSA-N 6-amino-4-(3-chloro-4-fluoroanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(N)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 MJOPKUFLFODTKP-UHFFFAOYSA-N 0.000 claims description 3
• JSRLAMXXELZKLJ-UHFFFAOYSA-N 6-amino-4-[3-(trifluoromethyl)anilino]quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C(F)(F)F)=C1 JSRLAMXXELZKLJ-UHFFFAOYSA-N 0.000 claims description 3
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
• 150000001408 amides Chemical class 0.000 claims description 3
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
• MDRKEUXLMJBPCY-UHFFFAOYSA-N 2-methoxyquinoline-3-carbonitrile Chemical compound C1=CC=C2C=C(C#N)C(OC)=NC2=C1 MDRKEUXLMJBPCY-UHFFFAOYSA-N 0.000 claims description 2
• GCNKUJAIEDINLA-UHFFFAOYSA-N 4-(2-hydroxy-6-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=C(C)C=CC=C1O GCNKUJAIEDINLA-UHFFFAOYSA-N 0.000 claims description 2
• WYUJPMJLGOVLKG-UHFFFAOYSA-N 4-(3,4-difluoroanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(F)=C1 WYUJPMJLGOVLKG-UHFFFAOYSA-N 0.000 claims description 2
• JCGYXRCAGZQKRK-UHFFFAOYSA-N 4-(3-bromo-4-fluoroanilino)-7-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound C=12C=C([N+]([O-])=O)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Br)=C1 JCGYXRCAGZQKRK-UHFFFAOYSA-N 0.000 claims description 2
• BOXDQGATHFGEIB-UHFFFAOYSA-N 4-(3-bromo-4-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(C)C(Br)=C1 BOXDQGATHFGEIB-UHFFFAOYSA-N 0.000 claims description 2
• VXMFIYMOOZZNJO-UHFFFAOYSA-N 4-(3-bromoanilino)-6,7,8-trimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1NC1=CC=CC(Br)=C1 VXMFIYMOOZZNJO-UHFFFAOYSA-N 0.000 claims description 2
• SNLXBZYKYWEIOV-UHFFFAOYSA-N 4-(3-bromoanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 SNLXBZYKYWEIOV-UHFFFAOYSA-N 0.000 claims description 2
• NUBVTRDETNNCGY-UHFFFAOYSA-N 4-(3-bromoanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound N#CC=1C=NC2=CC(OC)=CC=C2C=1NC1=CC=CC(Br)=C1 NUBVTRDETNNCGY-UHFFFAOYSA-N 0.000 claims description 2
• AFOMMVJBDXYOAA-UHFFFAOYSA-N 4-(3-bromoanilino)-8-methyl-6-nitroquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(C)=CC([N+]([O-])=O)=CC2=C1NC1=CC=CC(Br)=C1 AFOMMVJBDXYOAA-UHFFFAOYSA-N 0.000 claims description 2
• JPDTVCOEUUQNSS-UHFFFAOYSA-N 4-(3-bromophenoxy)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1OC1=CC=CC(Br)=C1 JPDTVCOEUUQNSS-UHFFFAOYSA-N 0.000 claims description 2
• VCNRVJKPJCKMIG-UHFFFAOYSA-N 4-(3-chloro-4-fluoroanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 VCNRVJKPJCKMIG-UHFFFAOYSA-N 0.000 claims description 2
• IJAFEDNMGMKIIZ-UHFFFAOYSA-N 4-(3-chloro-4-fluoroanilino)-7-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound C=12C=C([N+]([O-])=O)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 IJAFEDNMGMKIIZ-UHFFFAOYSA-N 0.000 claims description 2
• DUDXBCAIXIMAKI-UHFFFAOYSA-N 4-(3-chloro-4-hydroxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(O)C(Cl)=C1 DUDXBCAIXIMAKI-UHFFFAOYSA-N 0.000 claims description 2
• HLBGGOYPNRIHFH-UHFFFAOYSA-N 4-(3-chloroanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Cl)=C1 HLBGGOYPNRIHFH-UHFFFAOYSA-N 0.000 claims description 2
• FNRKKHMPSZQHEJ-UHFFFAOYSA-N 4-(3-chloroanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(Cl)=C1 FNRKKHMPSZQHEJ-UHFFFAOYSA-N 0.000 claims description 2
• CCECSDRSBLPTHW-UHFFFAOYSA-N 4-(3-cyanoanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(C#N)=C1 CCECSDRSBLPTHW-UHFFFAOYSA-N 0.000 claims description 2
• ADYHMPMHENUUSX-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-5,8-dimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=C(OC)C2=C1NC1=CC=C(C)C(O)=C1 ADYHMPMHENUUSX-UHFFFAOYSA-N 0.000 claims description 2
• HDYIFTHEJLLDHZ-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-6,7,8-trimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1NC1=CC=C(C)C(O)=C1 HDYIFTHEJLLDHZ-UHFFFAOYSA-N 0.000 claims description 2
• DLQVSGGYBADFFQ-UHFFFAOYSA-N 4-(3-iodoanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(I)=C1 DLQVSGGYBADFFQ-UHFFFAOYSA-N 0.000 claims description 2
• FMAZODAHMSMUNK-UHFFFAOYSA-N 4-(3-methylanilino)-6-nitroquinoline-3-carbonitrile Chemical compound CC1=CC=CC(NC=2C3=CC(=CC=C3N=CC=2C#N)[N+]([O-])=O)=C1 FMAZODAHMSMUNK-UHFFFAOYSA-N 0.000 claims description 2
• KBQXQEITHBAZNL-UHFFFAOYSA-N 4-(4-chloro-2-fluoro-5-hydroxyanilino)-5,8-dimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=C(OC)C2=C1NC1=CC(O)=C(Cl)C=C1F KBQXQEITHBAZNL-UHFFFAOYSA-N 0.000 claims description 2
• NXQUVEFCIXDBGX-UHFFFAOYSA-N 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6,7,8-trimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F NXQUVEFCIXDBGX-UHFFFAOYSA-N 0.000 claims description 2
• DCCQITVOSPOELC-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-6,7,8-trimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F DCCQITVOSPOELC-UHFFFAOYSA-N 0.000 claims description 2
• AZGVCABJHURYHG-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(Cl)C=C1F AZGVCABJHURYHG-UHFFFAOYSA-N 0.000 claims description 2
• PICBGXSASXFIAL-UHFFFAOYSA-N 4-(4-fluoroanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C=C1 PICBGXSASXFIAL-UHFFFAOYSA-N 0.000 claims description 2
• LMPUEJSCCKBFOV-UHFFFAOYSA-N 4-[3-(dimethylamino)anilino]-6,7,8-trimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1NC1=CC=CC(N(C)C)=C1 LMPUEJSCCKBFOV-UHFFFAOYSA-N 0.000 claims description 2
• GEUFKSXFZJFSDI-UHFFFAOYSA-N 4-[3-(hydroxymethyl)anilino]-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(CO)=C1 GEUFKSXFZJFSDI-UHFFFAOYSA-N 0.000 claims description 2
• YIUAOQMDEABCMH-UHFFFAOYSA-N 6,7-diethoxy-4-(3-fluoroanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(F)=C1 YIUAOQMDEABCMH-UHFFFAOYSA-N 0.000 claims description 2
• YXCSSHCCXLUHDG-UHFFFAOYSA-N 6,7-dimethoxy-4-(2-methylanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC=C1C YXCSSHCCXLUHDG-UHFFFAOYSA-N 0.000 claims description 2
• WEOXCMIQDJTOOP-UHFFFAOYSA-N 6,7-dimethoxy-4-(3-nitroanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC([N+]([O-])=O)=C1 WEOXCMIQDJTOOP-UHFFFAOYSA-N 0.000 claims description 2
• WMIBAZLHGIVWSU-UHFFFAOYSA-N 6-amino-4-(3-bromo-4-fluoroanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(N)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Br)=C1 WMIBAZLHGIVWSU-UHFFFAOYSA-N 0.000 claims description 2
• IUHXMKMPNZOIIR-UHFFFAOYSA-N 6-amino-4-(3-chloroanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Cl)=C1 IUHXMKMPNZOIIR-UHFFFAOYSA-N 0.000 claims description 2
• PDQUVNBKITWFNZ-UHFFFAOYSA-N 6-amino-4-(3-cyanoanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#N)=C1 PDQUVNBKITWFNZ-UHFFFAOYSA-N 0.000 claims description 2
• OXXUZYBVAKGKQB-UHFFFAOYSA-N 6-amino-4-(3-methoxyanilino)quinoline-3-carbonitrile Chemical compound COC1=CC=CC(NC=2C3=CC(N)=CC=C3N=CC=2C#N)=C1 OXXUZYBVAKGKQB-UHFFFAOYSA-N 0.000 claims description 2
• PNHLUCIDSVSCDW-UHFFFAOYSA-N 6-amino-4-(3-methylanilino)quinoline-3-carbonitrile Chemical compound CC1=CC=CC(NC=2C3=CC(N)=CC=C3N=CC=2C#N)=C1 PNHLUCIDSVSCDW-UHFFFAOYSA-N 0.000 claims description 2
• SIBQYOKZVKAXSA-UHFFFAOYSA-N 6-amino-4-(4-bromoanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=C(Br)C=C1 SIBQYOKZVKAXSA-UHFFFAOYSA-N 0.000 claims description 2
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• 150000002367 halogens Chemical class 0.000 claims description 2
• XNWKTBYXWIDLCZ-UHFFFAOYSA-N n-[3-cyano-4-(3-fluoroanilino)quinolin-6-yl]prop-2-enamide Chemical compound FC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 XNWKTBYXWIDLCZ-UHFFFAOYSA-N 0.000 claims description 2
• PLQLHGCLAWKBJG-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-7-methoxyquinolin-6-yl]but-2-ynamide Chemical compound C=12C=C(NC(=O)C#CC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 PLQLHGCLAWKBJG-UHFFFAOYSA-N 0.000 claims description 2
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• NHMLTTGVAYCKEO-UHFFFAOYSA-N n-[3-cyano-4-(3,4-dibromoanilino)quinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=C(Br)C(Br)=C1 NHMLTTGVAYCKEO-UHFFFAOYSA-N 0.000 claims 1
• YPKIJBWMDLKPTG-UHFFFAOYSA-N n-[3-cyano-4-(3,4-difluoroanilino)quinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(F)=C1 YPKIJBWMDLKPTG-UHFFFAOYSA-N 0.000 claims 1
• SQGPYBQAQIKBQS-UHFFFAOYSA-N n-[3-cyano-4-(3,4-difluoroanilino)quinolin-6-yl]prop-2-enamide Chemical compound C1=C(F)C(F)=CC=C1NC1=C(C#N)C=NC2=CC=C(NC(=O)C=C)C=C12 SQGPYBQAQIKBQS-UHFFFAOYSA-N 0.000 claims 1
• RLAZEQDNCUQRSX-UHFFFAOYSA-N n-[3-cyano-4-(3-cyanoanilino)quinolin-6-yl]-4-piperidin-1-ylbut-2-ynamide Chemical compound C1CCCCN1CC#CC(=O)NC(C=C12)=CC=C1N=CC(C#N)=C2NC1=CC=CC(C#N)=C1 RLAZEQDNCUQRSX-UHFFFAOYSA-N 0.000 claims 1
• VMWRFOQWNJQIMZ-UHFFFAOYSA-N n-[3-cyano-4-(3-cyanoanilino)quinolin-6-yl]prop-2-enamide Chemical compound C12=CC(NC(=O)C=C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#N)=C1 VMWRFOQWNJQIMZ-UHFFFAOYSA-N 0.000 claims 1
• BBBFROLYSXGUOP-UHFFFAOYSA-N n-[3-cyano-4-(3-ethynylanilino)quinolin-6-yl]-4-piperidin-1-ylbut-2-ynamide Chemical compound C1CCCCN1CC#CC(=O)NC(C=C12)=CC=C1N=CC(C#N)=C2NC1=CC=CC(C#C)=C1 BBBFROLYSXGUOP-UHFFFAOYSA-N 0.000 claims 1
• WFMBJUVKYJBICW-UHFFFAOYSA-N n-[3-cyano-4-(3-ethynylanilino)quinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#C)=C1 WFMBJUVKYJBICW-UHFFFAOYSA-N 0.000 claims 1
• WQTFCVASSZGLCT-UHFFFAOYSA-N n-[3-cyano-4-(3-ethynylanilino)quinolin-6-yl]prop-2-enamide Chemical compound C12=CC(NC(=O)C=C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#C)=C1 WQTFCVASSZGLCT-UHFFFAOYSA-N 0.000 claims 1
• DMSXOBAZCDAXLQ-UHFFFAOYSA-N n-[3-cyano-4-(3-iodoanilino)quinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(I)=C1 DMSXOBAZCDAXLQ-UHFFFAOYSA-N 0.000 claims 1
• RKKMOSSRGMBZAO-UHFFFAOYSA-N n-[3-cyano-4-(3-iodoanilino)quinolin-6-yl]prop-2-enamide Chemical compound IC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 RKKMOSSRGMBZAO-UHFFFAOYSA-N 0.000 claims 1
• VYLDYNHWUMJQMD-UHFFFAOYSA-N n-[3-cyano-4-(3-methoxyanilino)quinolin-6-yl]-4-piperidin-1-ylbut-2-ynamide Chemical compound COC1=CC=CC(NC=2C3=CC(NC(=O)C#CCN4CCCCC4)=CC=C3N=CC=2C#N)=C1 VYLDYNHWUMJQMD-UHFFFAOYSA-N 0.000 claims 1
• HMNIDDVKONQLPW-UHFFFAOYSA-N n-[3-cyano-4-(3-methoxyanilino)quinolin-6-yl]but-2-ynamide Chemical compound COC1=CC=CC(NC=2C3=CC(NC(=O)C#CC)=CC=C3N=CC=2C#N)=C1 HMNIDDVKONQLPW-UHFFFAOYSA-N 0.000 claims 1
• JEVROOVJYXQOEZ-UHFFFAOYSA-N n-[3-cyano-4-(3-methoxyanilino)quinolin-6-yl]prop-2-enamide Chemical compound COC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 JEVROOVJYXQOEZ-UHFFFAOYSA-N 0.000 claims 1
• NOPOIBJRWQZCGR-UHFFFAOYSA-N n-[3-cyano-4-(3-methylanilino)quinolin-6-yl]prop-2-enamide Chemical compound CC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 NOPOIBJRWQZCGR-UHFFFAOYSA-N 0.000 claims 1
• MQWPQDJSSWDVTQ-UHFFFAOYSA-N n-[3-cyano-4-(3-propan-2-ylanilino)quinolin-6-yl]prop-2-enamide Chemical compound CC(C)C1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 MQWPQDJSSWDVTQ-UHFFFAOYSA-N 0.000 claims 1
• QSMHWFXKNHCJSQ-UHFFFAOYSA-N n-[3-cyano-4-[3-(dimethylamino)anilino]quinolin-6-yl]prop-2-enamide Chemical compound CN(C)C1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 QSMHWFXKNHCJSQ-UHFFFAOYSA-N 0.000 claims 1
• VVNVIMKVRAEOEX-UHFFFAOYSA-N n-[3-cyano-4-[3-(trifluoromethyl)anilino]quinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C(F)(F)F)=C1 VVNVIMKVRAEOEX-UHFFFAOYSA-N 0.000 claims 1
• JSPHYZXDFYTYMG-UHFFFAOYSA-N n-[3-cyano-4-[4-(dimethylamino)anilino]quinolin-6-yl]prop-2-enamide Chemical compound C1=CC(N(C)C)=CC=C1NC1=C(C#N)C=NC2=CC=C(NC(=O)C=C)C=C12 JSPHYZXDFYTYMG-UHFFFAOYSA-N 0.000 claims 1
• IUYSZSPQSWJCLI-UHFFFAOYSA-N n-[4-(3-bromo-4-fluoroanilino)-3-cyano-7-methoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound C=12C=C(NC(=O)C=CCN(C)C)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Br)=C1 IUYSZSPQSWJCLI-UHFFFAOYSA-N 0.000 claims 1
• AKTAELVLHHYTPP-UHFFFAOYSA-N n-[4-(3-bromo-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-(diethylamino)but-2-enamide Chemical compound C12=CC(NC(=O)C=CCN(CC)CC)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Br)=C1 AKTAELVLHHYTPP-UHFFFAOYSA-N 0.000 claims 1
• OFGJOXKWOLGBRC-UHFFFAOYSA-N n-[4-(3-bromo-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound C12=CC(NC(=O)C=CCN(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Br)=C1 OFGJOXKWOLGBRC-UHFFFAOYSA-N 0.000 claims 1
• AHFLCVUUMDIYOY-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-7-ethoxyquinolin-6-yl]-4-(diethylamino)but-2-enamide Chemical compound C=12C=C(NC(=O)C=CCN(CC)CC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 AHFLCVUUMDIYOY-UHFFFAOYSA-N 0.000 claims 1
• XVHPHLVYCRDHSU-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-7-methoxyquinolin-6-yl]-4-(dimethylamino)but-2-ynamide Chemical compound C=12C=C(NC(=O)C#CCN(C)C)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 XVHPHLVYCRDHSU-UHFFFAOYSA-N 0.000 claims 1
• QWSSCGSSNDSGPP-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-7-methoxyquinolin-6-yl]-4-chlorobut-2-enamide Chemical compound C=12C=C(NC(=O)C=CCCl)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 QWSSCGSSNDSGPP-UHFFFAOYSA-N 0.000 claims 1
• HKLOKSUROGEMSK-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-7-methoxyquinolin-6-yl]prop-2-enamide Chemical compound C=12C=C(NC(=O)C=C)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 HKLOKSUROGEMSK-UHFFFAOYSA-N 0.000 claims 1
• CQFOPPHLPZNBKO-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-2-(morpholin-4-ylmethyl)prop-2-enamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C(=C)CN4CCOCC4)=CC=C3N=CC=2C#N)=C1 CQFOPPHLPZNBKO-UHFFFAOYSA-N 0.000 claims 1
• PTSZXFBVOGOHCV-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-2-chloroacetamide Chemical compound C12=CC(NC(=O)CCl)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 PTSZXFBVOGOHCV-UHFFFAOYSA-N 0.000 claims 1
• UYTOXOMHJMCOKH-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-(diethylamino)but-2-ynamide Chemical compound C12=CC(NC(=O)C#CCN(CC)CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 UYTOXOMHJMCOKH-UHFFFAOYSA-N 0.000 claims 1
• NYRBHASTRFCNHY-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-(dipropylamino)but-2-ynamide Chemical compound C12=CC(NC(=O)C#CCN(CCC)CCC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 NYRBHASTRFCNHY-UHFFFAOYSA-N 0.000 claims 1
• MXBVVVDUUIDCNR-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-methoxybut-2-ynamide Chemical compound C12=CC(NC(=O)C#CCOC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 MXBVVVDUUIDCNR-UHFFFAOYSA-N 0.000 claims 1
• KGUJQEYRHHBQRF-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]acetamide Chemical compound C12=CC(NC(=O)C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 KGUJQEYRHHBQRF-UHFFFAOYSA-N 0.000 claims 1
• JKBHSBZUZPGJAH-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]butanamide Chemical compound C12=CC(NC(=O)CCC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 JKBHSBZUZPGJAH-UHFFFAOYSA-N 0.000 claims 1
• MSLIBSZZLAWHQM-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]prop-2-enamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 MSLIBSZZLAWHQM-UHFFFAOYSA-N 0.000 claims 1
• QAIWBHUZZZOVEO-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]propanamide Chemical compound C12=CC(NC(=O)CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 QAIWBHUZZZOVEO-UHFFFAOYSA-N 0.000 claims 1
• VHGGLPYMJXZJFI-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-6-yl]-4-methoxybut-2-enamide Chemical compound C12=CC(NC(=O)C=CCOC)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 VHGGLPYMJXZJFI-UHFFFAOYSA-N 0.000 claims 1
• GPLSEURFJLQXHR-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 GPLSEURFJLQXHR-UHFFFAOYSA-N 0.000 claims 1
• CYCQVROTABWGKI-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]prop-2-enamide Chemical compound C1=C(Cl)C(F)=CC=C1NC1=C(C#N)C=NC2=CC=C(NC(=O)C=C)C=C12 CYCQVROTABWGKI-UHFFFAOYSA-N 0.000 claims 1
• SFXWFZYYIXZARH-UHFFFAOYSA-N n-[4-(3-chloroanilino)-3-cyanoquinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Cl)=C1 SFXWFZYYIXZARH-UHFFFAOYSA-N 0.000 claims 1
• GASFMMJWWWYIBV-UHFFFAOYSA-N n-[4-(3-chloroanilino)-3-cyanoquinolin-6-yl]prop-2-enamide Chemical compound ClC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 GASFMMJWWWYIBV-UHFFFAOYSA-N 0.000 claims 1
• HZFFAOYHSJFYAC-UHFFFAOYSA-N n-[4-(4-bromoanilino)-3-cyanoquinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=C(Br)C=C1 HZFFAOYHSJFYAC-UHFFFAOYSA-N 0.000 claims 1
• JQOCJKUVECLNAC-UHFFFAOYSA-N n-[4-(4-bromoanilino)-3-cyanoquinolin-6-yl]prop-2-enamide Chemical compound C1=CC(Br)=CC=C1NC1=C(C#N)C=NC2=CC=C(NC(=O)C=C)C=C12 JQOCJKUVECLNAC-UHFFFAOYSA-N 0.000 claims 1
• 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
• 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims 1
• WMOZUHUKRDBJEF-UHFFFAOYSA-N s-[[3-[(3-cyano-6,7-dimethoxyquinolin-4-yl)amino]phenyl]methyl] ethanethioate Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(CSC(C)=O)=C1 WMOZUHUKRDBJEF-UHFFFAOYSA-N 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 524
• 239000007787 solid Substances 0.000 description 374
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• 239000000243 solution Substances 0.000 description 293
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• 238000001819 mass spectrum Methods 0.000 description 181
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 165
• 239000002904 solvent Substances 0.000 description 161
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• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 151
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 151
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• 239000000047 product Substances 0.000 description 91
• AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 88
• 239000012044 organic layer Substances 0.000 description 81
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• ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 64
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• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 56
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
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• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 34
• YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 32
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• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 27
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
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• 239000012258 stirred mixture Substances 0.000 description 24
• 239000012267 brine Substances 0.000 description 23
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
• 239000012442 inert solvent Substances 0.000 description 22
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• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
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• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 19
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• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 17
• 239000000463 material Substances 0.000 description 17
• 150000008064 anhydrides Chemical class 0.000 description 16
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