TW201109323A - Heterocyclic compounds - Google Patents

Info

Publication number

TW201109323A

TW201109323A TW099126390A TW99126390A TW201109323A TW 201109323 A TW201109323 A TW 201109323A TW 099126390 A TW099126390 A TW 099126390A TW 99126390 A TW99126390 A TW 99126390A TW 201109323 A TW201109323 A TW 201109323A

Authority

TW

Taiwan

Prior art keywords

phenyl

ethyl

trifluoromethyl

hydroxy

hexahydropyridine

Prior art date

2009-08-07

Links

• Espacenet
• Global Dossier
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• 150000002391 heterocyclic compounds Chemical class 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 270
• 150000003839 salts Chemical class 0.000 claims abstract description 122
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 29
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 17
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 401
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 287
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 256
• -1 4-oxazolyl Chemical group 0.000 claims description 155
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 110
• 125000000217 alkyl group Chemical group 0.000 claims description 105
• 239000002253 acid Substances 0.000 claims description 80
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 67
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 52
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 44
• 125000001424 substituent group Chemical group 0.000 claims description 41
• 125000004122 cyclic group Chemical group 0.000 claims description 36
• 125000003545 alkoxy group Chemical group 0.000 claims description 34
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
• 239000003814 drug Substances 0.000 claims description 25
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 125000005842 heteroatom Chemical group 0.000 claims description 20
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 19
• 125000001188 haloalkyl group Chemical group 0.000 claims description 19
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
• 239000007789 gas Substances 0.000 claims description 18
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 18
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 16
• 125000001544 thienyl group Chemical group 0.000 claims description 15
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 14
• 125000003118 aryl group Chemical group 0.000 claims description 14
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 14
• 239000000126 substance Substances 0.000 claims description 14
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
• 125000004432 carbon atom Chemical group C* 0.000 claims description 12
• 229940079593 drug Drugs 0.000 claims description 12
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• 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 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 125000005843 halogen group Chemical group 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 229910052707 ruthenium Inorganic materials 0.000 claims description 9
• 125000004429 atom Chemical group 0.000 claims description 8
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 8
• VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 claims description 7
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 7
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• 239000001257 hydrogen Substances 0.000 claims description 6
• 208000027866 inflammatory disease Diseases 0.000 claims description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• XJLSEXAGTJCILF-UHFFFAOYSA-N nipecotic acid Chemical compound OC(=O)C1CCCNC1 XJLSEXAGTJCILF-UHFFFAOYSA-N 0.000 claims description 5
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
• 208000037976 chronic inflammation Diseases 0.000 claims description 3
• 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 3
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
• 229910052762 osmium Inorganic materials 0.000 claims description 3
• SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 3
• DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 3
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 2
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• IEMGWBMVQLVHEY-UHFFFAOYSA-N ethyl 2-(3-amino-6,7-dihydro-5h-cyclopenta[b]pyridin-7-yl)acetate Chemical compound NC1=CN=C2C(CC(=O)OCC)CCC2=C1 IEMGWBMVQLVHEY-UHFFFAOYSA-N 0.000 claims description 2
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 2
• 235000019260 propionic acid Nutrition 0.000 claims description 2
• 229910052705 radium Inorganic materials 0.000 claims description 2
• 150000001735 carboxylic acids Chemical class 0.000 claims 6
• 201000006747 infectious mononucleosis Diseases 0.000 claims 3
• 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims 2
• FTIRVEBTARAWRH-UHFFFAOYSA-N 1-[2-hydroxy-2-[4-[5-(5-phenyl-4-propyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]pyrrolidine-3-carboxylic acid Chemical compound CCCC=1C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2CC(CC2)C(O)=O)=NOC=1C1=CC=CC=C1 FTIRVEBTARAWRH-UHFFFAOYSA-N 0.000 claims 2
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
• WQOAODKWNVPLPY-RHSMWYFYSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[5-propan-2-yl-4-(trifluoromethyl)-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound FC(F)(F)C1=C(C(C)C)ON=C1C1=NC(C=2C=CC(=CC=2)[C@H](O)CN2C[C@@H](CC(O)=O)CCC2)=NO1 WQOAODKWNVPLPY-RHSMWYFYSA-N 0.000 claims 1
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• IXOFDKUWTXPQFC-UHFFFAOYSA-N 3-(trifluoromethyl)-1,2-oxazole Chemical compound FC(F)(F)C=1C=CON=1 IXOFDKUWTXPQFC-UHFFFAOYSA-N 0.000 claims 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims 1
• 125000005605 benzo group Chemical group 0.000 claims 1
• 125000002720 diazolyl group Chemical group 0.000 claims 1
• 239000011737 fluorine Substances 0.000 claims 1
• 125000001207 fluorophenyl group Chemical group 0.000 claims 1
• 150000004000 hexols Chemical class 0.000 claims 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
• HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims 1
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 1
• 235000001968 nicotinic acid Nutrition 0.000 claims 1
• 239000011664 nicotinic acid Substances 0.000 claims 1
• 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims 1
• 230000001568 sexual effect Effects 0.000 claims 1
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
• 239000000829 suppository Substances 0.000 claims 1
• 125000004297 tetrahydropyrrol-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 66
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 32
• 201000010099 disease Diseases 0.000 abstract description 29
• 208000019553 vascular disease Diseases 0.000 abstract description 8
• 230000001225 therapeutic effect Effects 0.000 abstract description 7
• 102100025750 Sphingosine 1-phosphate receptor 1 Human genes 0.000 abstract description 4
• 101710155454 Sphingosine 1-phosphate receptor 1 Proteins 0.000 abstract description 4
• 229910052760 oxygen Inorganic materials 0.000 abstract description 4
• 239000000556 agonist Substances 0.000 abstract description 3
• 208000035475 disorder Diseases 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 292
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 185
• 239000011541 reaction mixture Substances 0.000 description 163
• 238000004128 high performance liquid chromatography Methods 0.000 description 148
• 239000000203 mixture Substances 0.000 description 141
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 130
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 128
• 229910001868 water Inorganic materials 0.000 description 124
• 235000019439 ethyl acetate Nutrition 0.000 description 119
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 90
• 238000002360 preparation method Methods 0.000 description 88
• 238000006243 chemical reaction Methods 0.000 description 83
• 239000002904 solvent Substances 0.000 description 83
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 80
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 66
• 206010057190 Respiratory tract infections Diseases 0.000 description 62
• 239000000243 solution Substances 0.000 description 57
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 56
• 239000002585 base Substances 0.000 description 56
• 238000010521 absorption reaction Methods 0.000 description 53
• 239000012044 organic layer Substances 0.000 description 51
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 49
• 239000000651 prodrug Substances 0.000 description 49
• 229940002612 prodrug Drugs 0.000 description 49
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
• 239000000047 product Substances 0.000 description 46
• 230000002829 reductive effect Effects 0.000 description 42
• 239000007787 solid Substances 0.000 description 40
• 238000004458 analytical method Methods 0.000 description 38
• 238000005481 NMR spectroscopy Methods 0.000 description 33
• 239000000543 intermediate Substances 0.000 description 33
• 239000012071 phase Substances 0.000 description 31
• 238000005160 1H NMR spectroscopy Methods 0.000 description 27
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
• 239000003921 oil Substances 0.000 description 26
• 235000019198 oils Nutrition 0.000 description 26
• 101150041968 CDC13 gene Proteins 0.000 description 23
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 23
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 23
• 239000010410 layer Substances 0.000 description 23
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 22
• 230000014759 maintenance of location Effects 0.000 description 22
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 21
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
• 230000000694 effects Effects 0.000 description 20
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 19
• 229920006395 saturated elastomer Polymers 0.000 description 19
• 239000003153 chemical reaction reagent Substances 0.000 description 18
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 18
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 17
• 150000001412 amines Chemical class 0.000 description 17
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 17
• JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical group CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 15
• 238000003786 synthesis reaction Methods 0.000 description 15
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 14
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 14
• 239000002245 particle Substances 0.000 description 14
• 102000005962 receptors Human genes 0.000 description 14
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• 150000001408 amides Chemical class 0.000 description 13
• 230000015572 biosynthetic process Effects 0.000 description 13
• 239000003795 chemical substances by application Substances 0.000 description 13
• 210000004027 cell Anatomy 0.000 description 12
• MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 12
• 125000004494 ethyl ester group Chemical group 0.000 description 12
• QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 12
• 239000000463 material Substances 0.000 description 12
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
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• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
• 230000001363 autoimmune Effects 0.000 description 11
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• 239000003643 water by type Substances 0.000 description 11
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
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• 229910052799 carbon Inorganic materials 0.000 description 10
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• 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
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• 230000009467 reduction Effects 0.000 description 10
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• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
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• 239000000706 filtrate Substances 0.000 description 8
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• 229910002027 silica gel Inorganic materials 0.000 description 8
• 239000007858 starting material Substances 0.000 description 8
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• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
• 241001465754 Metazoa Species 0.000 description 7
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• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 7
• 239000007864 aqueous solution Substances 0.000 description 7
• 230000008878 coupling Effects 0.000 description 7
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