IL129394A

IL129394A - Amino-alkaline phosphonic acids are converted

Amino-alkaline phosphonic acids are converted

Info

Publication number: IL129394A
Authority: IL; Israel
Prior art keywords: dioxo; tetrahydroquinoxalin; ylmethyl; acid; nitro
Prior art date: 1996-10-24

Application number

IL12939497A

Other languages

English (en)

Hebrew (he)

Other versions

IL129394A0 (en

Original Assignee

Novartis Ag

Priority date

1996-10-24

Filing date

1997-10-22

Publication date

2002-05-23

1997-10-22 Application filed by Novartis Ag filed Critical Novartis Ag

2000-02-17 Publication of IL129394A0 publication Critical patent/IL129394A0/xx

2002-05-23 Publication of IL129394A publication Critical patent/IL129394A/en

Links

150000003009 phosphonic acids Chemical class 0.000 title description 2
-1 methylene, 3-hydroxybenzylidene, 3-methoxybenzylidene, 3-pyridylmethylene, ethylene, oxoethylene, ethylidene, 1, 3-propylene Chemical group 0.000 claims abstract description 165
150000001875 compounds Chemical class 0.000 claims abstract description 133
125000001118 alkylidene group Chemical group 0.000 claims abstract description 77
150000003839 salts Chemical class 0.000 claims abstract description 59
239000001257 hydrogen Substances 0.000 claims abstract description 53
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 53
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 45
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 43
125000000217 alkyl group Chemical group 0.000 claims abstract description 39
150000002431 hydrogen Chemical class 0.000 claims abstract description 35
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 34
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 21
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 20
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 19
125000001931 aliphatic group Chemical group 0.000 claims abstract description 18
229910052736 halogen Inorganic materials 0.000 claims abstract description 18
150000002367 halogens Chemical class 0.000 claims abstract description 18
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 16
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 16
229910052794 bromium Inorganic materials 0.000 claims abstract description 16
125000004980 cyclopropylene group Chemical group 0.000 claims abstract description 13
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 7
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 7
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims abstract description 5
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims abstract description 5
239000002253 acid Substances 0.000 claims description 68
239000000203 mixture Substances 0.000 claims description 43
125000002947 alkylene group Chemical group 0.000 claims description 27
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 26
241001484259 Lacuna Species 0.000 claims description 22
125000006239 protecting group Chemical group 0.000 claims description 20
238000000034 method Methods 0.000 claims description 19
150000003254 radicals Chemical class 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 11
239000000825 pharmaceutical preparation Substances 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
125000002993 cycloalkylene group Chemical group 0.000 claims description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical group C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
125000004957 naphthylene group Chemical group 0.000 claims description 5
UYLUJGRCKKSWHS-UHFFFAOYSA-N prop-1-en-1-one Chemical group CC=C=O UYLUJGRCKKSWHS-UHFFFAOYSA-N 0.000 claims description 5
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
239000005977 Ethylene Substances 0.000 claims description 4
102000018899 Glutamate Receptors Human genes 0.000 claims description 4
108010027915 Glutamate Receptors Proteins 0.000 claims description 4
125000005236 alkanoylamino group Chemical group 0.000 claims description 4
125000004450 alkenylene group Chemical group 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
FBWJHGIUUCOZRM-UHFFFAOYSA-N cyclopropylphosphonic acid Chemical compound OP(O)(=O)C1CC1 FBWJHGIUUCOZRM-UHFFFAOYSA-N 0.000 claims description 4
WWQAGDWTJOKFQB-UHFFFAOYSA-N penta-1,2,3-triene Chemical group CC=C=C=C WWQAGDWTJOKFQB-UHFFFAOYSA-N 0.000 claims description 4
239000000969 carrier Substances 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
241001465754 Metazoa Species 0.000 claims description 2
GZTLDIMDXMFIAC-UHFFFAOYSA-N [1-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]cyclopropyl]phosphonic acid Chemical compound C=1C(Br)=CC=2NC(=O)C(=O)NC=2C=1CNC1(P(O)(=O)O)CC1 GZTLDIMDXMFIAC-UHFFFAOYSA-N 0.000 claims description 2
ZYPSIDXTXGSMDP-UHFFFAOYSA-N [2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]-2-oxoethyl]phosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C=C2CNC(=O)CP(O)(=O)O ZYPSIDXTXGSMDP-UHFFFAOYSA-N 0.000 claims description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
229940058182 aminoethylphosphinic acid Drugs 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
230000001575 pathological effect Effects 0.000 claims description 2
SIUHDQKKTWZIQP-UHFFFAOYSA-N piperidin-4-ylphosphonic acid Chemical compound OP(O)(=O)C1CCNCC1 SIUHDQKKTWZIQP-UHFFFAOYSA-N 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
GRKSQRAVWODMGW-UHFFFAOYSA-N ethylphosphonic acid Chemical compound [CH2]CP(O)(O)=O GRKSQRAVWODMGW-UHFFFAOYSA-N 0.000 claims 9
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 claims 2
MIVCAFPOXPFYDI-UHFFFAOYSA-N 2-[acetyl-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]amino]ethylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C=C2CN(CCP(O)(O)=O)C(=O)C MIVCAFPOXPFYDI-UHFFFAOYSA-N 0.000 claims 1
PSYSVMKGZBEORX-UHFFFAOYSA-N 2-[benzyl-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]amino]ethylphosphonic acid Chemical compound C=1C([N+]([O-])=O)=CC=2NC(=O)C(=O)NC=2C=1CN(CCP(O)(=O)O)CC1=CC=CC=C1 PSYSVMKGZBEORX-UHFFFAOYSA-N 0.000 claims 1
ONYWCBASWXPZIF-UHFFFAOYSA-N 5-[[4-(diethoxyphosphorylmethyl)anilino]methyl]-7-nitro-1,4-dihydroquinoxaline-2,3-dione Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1NCC1=CC([N+]([O-])=O)=CC2=C1NC(=O)C(=O)N2 ONYWCBASWXPZIF-UHFFFAOYSA-N 0.000 claims 1
DXBFLGPYRWBEON-UHFFFAOYSA-N O=C1NC2=CC(=CC(=C2NC1=O)CNOP(O)(=O)CC(C)(C)O)[N+](=O)[O-] Chemical compound O=C1NC2=CC(=CC(=C2NC1=O)CNOP(O)(=O)CC(C)(C)O)[N+](=O)[O-] DXBFLGPYRWBEON-UHFFFAOYSA-N 0.000 claims 1
WHLUZDISMJQMGN-UHFFFAOYSA-N [1-(2-chlorophenyl)-2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]ethyl]phosphonic acid Chemical compound C=1C([N+]([O-])=O)=CC=2NC(=O)C(=O)NC=2C=1CNCC(P(O)(=O)O)C1=CC=CC=C1Cl WHLUZDISMJQMGN-UHFFFAOYSA-N 0.000 claims 1
ZWZVZTHITHMFLN-UHFFFAOYSA-N [1-(3-methoxyphenyl)-2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]ethyl]phosphonic acid Chemical compound COC1=CC=CC(C(CNCC=2C=3NC(=O)C(=O)NC=3C=C(C=2)[N+]([O-])=O)P(O)(O)=O)=C1 ZWZVZTHITHMFLN-UHFFFAOYSA-N 0.000 claims 1
UUIWLVZPDQFCPP-UHFFFAOYSA-N [1-(4-methoxyphenyl)-2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]ethyl]phosphonic acid Chemical compound C1=CC(OC)=CC=C1C(P(O)(O)=O)CNCC1=CC([N+]([O-])=O)=CC2=C1NC(=O)C(=O)N2 UUIWLVZPDQFCPP-UHFFFAOYSA-N 0.000 claims 1
IKJACYXTXDUKTH-UHFFFAOYSA-N [1-(4-methylphenyl)-2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]ethyl]phosphonic acid Chemical compound C1=CC(C)=CC=C1C(P(O)(O)=O)CNCC1=CC([N+]([O-])=O)=CC2=C1NC(=O)C(=O)N2 IKJACYXTXDUKTH-UHFFFAOYSA-N 0.000 claims 1
VAWWOZTXGXEBQT-UHFFFAOYSA-N [1-(furan-2-yl)-2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]ethyl]phosphonic acid Chemical compound C=1C([N+]([O-])=O)=CC=2NC(=O)C(=O)NC=2C=1CNCC(P(O)(=O)O)C1=CC=CO1 VAWWOZTXGXEBQT-UHFFFAOYSA-N 0.000 claims 1
GHYIICGXAVDEEQ-UHFFFAOYSA-N [2-(2-methoxyphenyl)-2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]ethyl]phosphonic acid Chemical compound COC1=CC=CC=C1C(CP(O)(O)=O)NCC1=CC([N+]([O-])=O)=CC2=C1NC(=O)C(=O)N2 GHYIICGXAVDEEQ-UHFFFAOYSA-N 0.000 claims 1
KVDQQUPSTWQIFE-UHFFFAOYSA-N [2-(4-fluorophenyl)-2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]ethyl]phosphonic acid Chemical compound C=1C([N+]([O-])=O)=CC=2NC(=O)C(=O)NC=2C=1CNC(CP(O)(=O)O)C1=CC=C(F)C=C1 KVDQQUPSTWQIFE-UHFFFAOYSA-N 0.000 claims 1
AQQNFWADZLJQER-UHFFFAOYSA-N [2-(4-methylphenyl)-2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]ethyl]phosphonic acid Chemical compound C1=CC(C)=CC=C1C(CP(O)(O)=O)NCC1=CC([N+]([O-])=O)=CC2=C1NC(=O)C(=O)N2 AQQNFWADZLJQER-UHFFFAOYSA-N 0.000 claims 1
HNDDDDVTFPAPCP-UHFFFAOYSA-N [2-[(7-chloro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]phenyl]phosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1NCC1=CC(Cl)=CC2=C1NC(=O)C(=O)N2 HNDDDDVTFPAPCP-UHFFFAOYSA-N 0.000 claims 1
FGBAYYWUPWHOSM-UHFFFAOYSA-N [2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]-1-phenylethyl]phosphonic acid Chemical compound C=1C([N+]([O-])=O)=CC=2NC(=O)C(=O)NC=2C=1CNCC(P(O)(=O)O)C1=CC=CC=C1 FGBAYYWUPWHOSM-UHFFFAOYSA-N 0.000 claims 1
YJZAUNIEICDTQU-UHFFFAOYSA-N [2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]cyclohexyl]phosphonic acid Chemical compound OP(O)(=O)C1CCCCC1NCC1=CC([N+]([O-])=O)=CC2=C1NC(=O)C(=O)N2 YJZAUNIEICDTQU-UHFFFAOYSA-N 0.000 claims 1
BPKBZWYRUMZASQ-UHFFFAOYSA-N [2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]phenyl]phosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1NCC1=CC([N+]([O-])=O)=CC2=C1NC(=O)C(=O)N2 BPKBZWYRUMZASQ-UHFFFAOYSA-N 0.000 claims 1
YKFXIXPHWMHGFH-UHFFFAOYSA-N [2-cyclohexyl-2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]ethyl]phosphonic acid Chemical compound C=1C([N+]([O-])=O)=CC=2NC(=O)C(=O)NC=2C=1CNC(CP(O)(=O)O)C1CCCCC1 YKFXIXPHWMHGFH-UHFFFAOYSA-N 0.000 claims 1
GONNEIKYHFCBGU-UHFFFAOYSA-N [2-methyl-2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]propyl]phosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C=C2CNC(C)(CP(O)(O)=O)C GONNEIKYHFCBGU-UHFFFAOYSA-N 0.000 claims 1
CYPZMRUQQQRAMY-UHFFFAOYSA-N [3-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]-3-oxoprop-1-enyl]phosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C=C2CNC(=O)C=CP(O)(=O)O CYPZMRUQQQRAMY-UHFFFAOYSA-N 0.000 claims 1
OQZDOXGUROQYME-UHFFFAOYSA-N [4-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]-4-oxobutyl]phosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C=C2CNC(=O)CCCP(O)(=O)O OQZDOXGUROQYME-UHFFFAOYSA-N 0.000 claims 1
XUKLLYLTRILNRP-UHFFFAOYSA-N [4-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]phenyl]methylphosphonic acid Chemical compound C1=CC(CP(O)(=O)O)=CC=C1NCC1=CC([N+]([O-])=O)=CC2=C1NC(=O)C(=O)N2 XUKLLYLTRILNRP-UHFFFAOYSA-N 0.000 claims 1
YEDFXUYTNVGXMI-UHFFFAOYSA-N [acetyl-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]amino]methylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CN(C(=O)C)CP(O)(O)=O YEDFXUYTNVGXMI-UHFFFAOYSA-N 0.000 claims 1
IGMCOMPQIJDGTG-UHFFFAOYSA-N [acetyl-[(7-chloro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]amino]methylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Cl)C=C2CN(C(=O)C)CP(O)(O)=O IGMCOMPQIJDGTG-UHFFFAOYSA-N 0.000 claims 1
ZSWDXFYLSPZCAS-UHFFFAOYSA-N [acetyl-[(7-fluoro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]amino]methylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(F)C=C2CN(C(=O)C)CP(O)(O)=O ZSWDXFYLSPZCAS-UHFFFAOYSA-N 0.000 claims 1
SOGYSBHHGXAEQM-UHFFFAOYSA-N [benzyl-(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)amino]methylphosphonic acid Chemical compound C=1C(Br)=CC=2NC(=O)C(=O)NC=2C=1N(CP(O)(=O)O)CC1=CC=CC=C1 SOGYSBHHGXAEQM-UHFFFAOYSA-N 0.000 claims 1
SGGXWHUGEWMJLD-UHFFFAOYSA-N [benzyl-(7-fluoro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)amino]methylphosphonic acid Chemical compound C=1C(F)=CC=2NC(=O)C(=O)NC=2C=1N(CP(O)(=O)O)CC1=CC=CC=C1 SGGXWHUGEWMJLD-UHFFFAOYSA-N 0.000 claims 1
YQLNBHKRXIKZPY-UHFFFAOYSA-N [benzyl-(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)amino]methylphosphonic acid Chemical compound C=1C([N+]([O-])=O)=CC=2NC(=O)C(=O)NC=2C=1N(CP(O)(=O)O)CC1=CC=CC=C1 YQLNBHKRXIKZPY-UHFFFAOYSA-N 0.000 claims 1
ABFMMCZFKUIJGQ-UHFFFAOYSA-N becampanel Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C=C2CNCP(O)(=O)O ABFMMCZFKUIJGQ-UHFFFAOYSA-N 0.000 claims 1
DSCKZQZZZRHKAF-UHFFFAOYSA-N benzyl-[[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]methyl]phosphinic acid Chemical compound C=1C([N+]([O-])=O)=CC=2NC(=O)C(=O)NC=2C=1CNCP(=O)(O)CC1=CC=CC=C1 DSCKZQZZZRHKAF-UHFFFAOYSA-N 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
AKWJYUMMADUPTI-UHFFFAOYSA-N methyl-[2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]-2-phenylethyl]phosphinic acid Chemical compound C=1C([N+]([O-])=O)=CC=2NC(=O)C(=O)NC=2C=1CNC(CP(O)(=O)C)C1=CC=CC=C1 AKWJYUMMADUPTI-UHFFFAOYSA-N 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 55
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
235000002639 sodium chloride Nutrition 0.000 description 48
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
239000000243 solution Substances 0.000 description 38
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 30
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
235000019439 ethyl acetate Nutrition 0.000 description 29
239000011541 reaction mixture Substances 0.000 description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
238000005160 1H NMR spectroscopy Methods 0.000 description 24
239000004480 active ingredient Substances 0.000 description 21
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
239000007787 solid Substances 0.000 description 20
239000002585 base Substances 0.000 description 18
239000013078 crystal Substances 0.000 description 18
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 18
239000012074 organic phase Substances 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
229910052943 magnesium sulfate Inorganic materials 0.000 description 15
235000019341 magnesium sulphate Nutrition 0.000 description 15
239000012267 brine Substances 0.000 description 14
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