CZ20033202A3 - Bicyklické heterocyklické sloučeniny obsahující dusík pro použití jako antibakteriální činidla - Google Patents

Info

Publication number

CZ20033202A3

CZ20033202A3 CZ20033202A CZ20033202A CZ20033202A3 CZ 20033202 A3 CZ20033202 A3 CZ 20033202A3 CZ 20033202 A CZ20033202 A CZ 20033202A CZ 20033202 A CZ20033202 A CZ 20033202A CZ 20033202 A3 CZ20033202 A3 CZ 20033202A3

Authority

CZ

Czechia

Prior art keywords

amino

alkyl

amide

oxo

dihydro

Prior art date

2001-05-25

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• 239000003242 anti bacterial agent Substances 0.000 title description 5
• 238000000034 method Methods 0.000 claims abstract description 162
• 241000124008 Mammalia Species 0.000 claims abstract description 9
• 208000035143 Bacterial infection Diseases 0.000 claims abstract description 7
• 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 7
• -1 amino, piperidyl Chemical group 0.000 claims description 394
• 150000001875 compounds Chemical class 0.000 claims description 249
• 125000000217 alkyl group Chemical group 0.000 claims description 202
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 86
• 229910052739 hydrogen Inorganic materials 0.000 claims description 80
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 77
• NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 58
• 150000001408 amides Chemical class 0.000 claims description 54
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 54
• 125000003277 amino group Chemical group 0.000 claims description 49
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 48
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 48
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 47
• 230000008569 process Effects 0.000 claims description 45
• 125000003118 aryl group Chemical group 0.000 claims description 43
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 42
• 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 42
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 41
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 40
• 239000001257 hydrogen Substances 0.000 claims description 39
• 229910052736 halogen Inorganic materials 0.000 claims description 36
• 239000002253 acid Substances 0.000 claims description 35
• VUHCPMIDSUGHNO-UHFFFAOYSA-N 6-methoxy-1,5-naphthyridin-4-amine Chemical compound N1=CC=C(N)C2=NC(OC)=CC=C21 VUHCPMIDSUGHNO-UHFFFAOYSA-N 0.000 claims description 33
• 150000002367 halogens Chemical class 0.000 claims description 32
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
• 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 31
• VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims description 29
• 229910005965 SO 2 Inorganic materials 0.000 claims description 26
• 125000001424 substituent group Chemical group 0.000 claims description 24
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
• 125000000623 heterocyclic group Chemical group 0.000 claims description 22
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 21
• 125000003342 alkenyl group Chemical group 0.000 claims description 20
• 125000004414 alkyl thio group Chemical group 0.000 claims description 20
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 19
• 125000003545 alkoxy group Chemical group 0.000 claims description 18
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 17
• 238000002360 preparation method Methods 0.000 claims description 17
• 229910052717 sulfur Inorganic materials 0.000 claims description 17
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
• 125000006574 non-aromatic ring group Chemical group 0.000 claims description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
• 125000005843 halogen group Chemical group 0.000 claims description 13
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 12
• 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 12
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
• 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 238000005984 hydrogenation reaction Methods 0.000 claims description 12
• 125000002252 acyl group Chemical group 0.000 claims description 11
• 125000004429 atom Chemical group 0.000 claims description 11
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
• 125000004043 oxo group Chemical group O=* 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical compound OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 claims description 9
• 125000004423 acyloxy group Chemical group 0.000 claims description 9
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 9
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 9
• 229910052727 yttrium Inorganic materials 0.000 claims description 9
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 7
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 6
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
• 150000005378 cyclohexanecarboxylic acids Chemical class 0.000 claims description 6
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 6
• 125000003282 alkyl amino group Chemical group 0.000 claims description 5
• 125000005647 linker group Chemical group 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
• 229910052721 tungsten Inorganic materials 0.000 claims description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
• 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims description 4
• 125000005035 acylthio group Chemical group 0.000 claims description 4
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
• 125000005605 benzo group Chemical group 0.000 claims description 4
• 239000003814 drug Substances 0.000 claims description 4
• 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
• 125000004432 carbon atom Chemical group C* 0.000 claims description 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 3
• 125000002950 monocyclic group Chemical group 0.000 claims description 3
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 3
• LASPDBMDWYKLQC-IYARVYRRSA-N COC1=CC2=C(C=C1)N=CC=C2NC(=O)[C@H]1CC[C@@H](CC1)NCC1=CC=C2SCC(=O)NC2=C1 Chemical compound COC1=CC2=C(C=C1)N=CC=C2NC(=O)[C@H]1CC[C@@H](CC1)NCC1=CC=C2SCC(=O)NC2=C1 LASPDBMDWYKLQC-IYARVYRRSA-N 0.000 claims description 2
• 125000004442 acylamino group Chemical group 0.000 claims description 2
• 125000005360 alkyl sulfoxide group Chemical group 0.000 claims description 2
• 125000000304 alkynyl group Chemical group 0.000 claims description 2
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
• 125000005361 aryl sulfoxide group Chemical group 0.000 claims description 2
• 125000005110 aryl thio group Chemical group 0.000 claims description 2
• 125000004104 aryloxy group Chemical group 0.000 claims description 2
• 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 2
• 150000003950 cyclic amides Chemical class 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
• 125000004468 heterocyclylthio group Chemical group 0.000 claims description 2
• 125000006413 ring segment Chemical group 0.000 claims description 2
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
• WWYLVEIKNRIFSD-UHFFFAOYSA-N n-(6-methoxy-1,5-naphthyridin-4-yl)cyclohexanecarboxamide Chemical compound C12=NC(OC)=CC=C2N=CC=C1NC(=O)C1CCCCC1 WWYLVEIKNRIFSD-UHFFFAOYSA-N 0.000 claims 3
• WOXWUZCRWJWTRT-UHFFFAOYSA-N 1-amino-1-cyclohexanecarboxylic acid Chemical compound OC(=O)C1(N)CCCCC1 WOXWUZCRWJWTRT-UHFFFAOYSA-N 0.000 claims 2
• ASFAFOSQXBRFMV-LJQANCHMSA-N 3-n-(2-benzyl-1,3-dihydroxypropan-2-yl)-1-n-[(1r)-1-(4-fluorophenyl)ethyl]-5-[methyl(methylsulfonyl)amino]benzene-1,3-dicarboxamide Chemical compound N([C@H](C)C=1C=CC(F)=CC=1)C(=O)C(C=1)=CC(N(C)S(C)(=O)=O)=CC=1C(=O)NC(CO)(CO)CC1=CC=CC=C1 ASFAFOSQXBRFMV-LJQANCHMSA-N 0.000 claims 2
• UDQAHFTWCBMBAL-UHFFFAOYSA-N 6,8-difluoroquinolin-4-amine Chemical compound C1=C(F)C=C2C(N)=CC=NC2=C1F UDQAHFTWCBMBAL-UHFFFAOYSA-N 0.000 claims 2
• JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims 2
• VLYZXDARBDJCPT-PEXQALLHSA-N (1s,3s,4s)-3-hydroxy-4-[(2-oxo-1h-pyrido[3,4-b][1,4]oxazin-7-yl)methylamino]cyclohexane-1-carboxylic acid Chemical compound O[C@H]1C[C@@H](C(O)=O)CC[C@@H]1NCC(N=C1)=CC2=C1OCC(=O)N2 VLYZXDARBDJCPT-PEXQALLHSA-N 0.000 claims 1
• YJGLLSACEYQDLT-LSJOCFKGSA-N (1s,3s,4s)-3-hydroxy-4-[(3-oxo-4h-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino]cyclohexane-1-carboxylic acid Chemical compound O[C@H]1C[C@@H](C(O)=O)CC[C@@H]1NCC1=CC=C(SCC(=O)N2)C2=N1 YJGLLSACEYQDLT-LSJOCFKGSA-N 0.000 claims 1
• LQPCQVDOJCRRRI-UHFFFAOYSA-N 1-(sulfonylamino)cyclohexane-1-carboxylic acid Chemical compound O=S(=O)=NC1(C(=O)O)CCCCC1 LQPCQVDOJCRRRI-UHFFFAOYSA-N 0.000 claims 1
• DKLKZOIVBZXREC-UHFFFAOYSA-N 2-aminocyclohexene-1-carboxylic acid Chemical compound NC1=C(C(O)=O)CCCC1 DKLKZOIVBZXREC-UHFFFAOYSA-N 0.000 claims 1
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
• XEKAWZARUWARND-UHFFFAOYSA-N 6h-oxazin-3-one Chemical compound O=C1NOCC=C1 XEKAWZARUWARND-UHFFFAOYSA-N 0.000 claims 1
• 239000005711 Benzoic acid Substances 0.000 claims 1
• PVJWKMPQWFTGDW-QAQDUYKDSA-N C1=C2N(C)C(=O)OC2=CC(CN[C@H]2CC[C@@H](CC2)C(=O)NC2=CC=NC3=CC=C(N=C32)OC)=C1 Chemical compound C1=C2N(C)C(=O)OC2=CC(CN[C@H]2CC[C@@H](CC2)C(=O)NC2=CC=NC3=CC=C(N=C32)OC)=C1 PVJWKMPQWFTGDW-QAQDUYKDSA-N 0.000 claims 1
• KLSTXOBNGOBMHF-JCNLHEQBSA-N C1=CC(O)=C2C(=O)NC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC2=C1 Chemical compound C1=CC(O)=C2C(=O)NC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC2=C1 KLSTXOBNGOBMHF-JCNLHEQBSA-N 0.000 claims 1
• WTLYHEBGJJAVMZ-WKILWMFISA-N C1=CC2=NSN=C2C=C1CN[C@H](CC1)CC[C@@H]1C(=O)NC1=CC=NC2=CC=C(OC)N=C21 Chemical compound C1=CC2=NSN=C2C=C1CN[C@H](CC1)CC[C@@H]1C(=O)NC1=CC=NC2=CC=C(OC)N=C21 WTLYHEBGJJAVMZ-WKILWMFISA-N 0.000 claims 1
• SCEYQRZPEASLEG-UPNAAVACSA-N COC1=CC2=C(C=C1)N=CC=C2C(O)C[C@H]1CC[C@@H](CC1)NCC1=CC2=C(SCC(=O)N2)C=C1 Chemical compound COC1=CC2=C(C=C1)N=CC=C2C(O)C[C@H]1CC[C@@H](CC1)NCC1=CC2=C(SCC(=O)N2)C=C1 SCEYQRZPEASLEG-UPNAAVACSA-N 0.000 claims 1
• VQDYYIZWEXWVDX-QAQDUYKDSA-N COC1=CC2=C(N=CC=C2NC(=O)[C@H]2CC[C@@H](CC2)NCC2=CC=C3SCC(=O)NC3=C2)C(F)=C1 Chemical compound COC1=CC2=C(N=CC=C2NC(=O)[C@H]2CC[C@@H](CC2)NCC2=CC=C3SCC(=O)NC3=C2)C(F)=C1 VQDYYIZWEXWVDX-QAQDUYKDSA-N 0.000 claims 1
• RONNYFTVWCSTTR-WKILWMFISA-N COC=1N=C2C(=CC=NC2=CC1)NC(=O)[C@@H]1CC[C@H](CC1)NCC=1C=CC2=C(N=NS2)C1 Chemical compound COC=1N=C2C(=CC=NC2=CC1)NC(=O)[C@@H]1CC[C@H](CC1)NCC=1C=CC2=C(N=NS2)C1 RONNYFTVWCSTTR-WKILWMFISA-N 0.000 claims 1
• VUWIHBMHDCCKDK-KESTWPANSA-N COc1ccc2nccc(C(=O)C[C@H]3CC[C@@H](CC3)NCc3ccc4OCCOc4c3)c2c1 Chemical compound COc1ccc2nccc(C(=O)C[C@H]3CC[C@@H](CC3)NCc3ccc4OCCOc4c3)c2c1 VUWIHBMHDCCKDK-KESTWPANSA-N 0.000 claims 1
• KXTMYJBJTDOVIC-NUDRXGSASA-N COc1ccc2nccc(C(O)C[C@H]3CC[C@@H](CC3)NCc3ccc4OCCOc4c3)c2c1 Chemical compound COc1ccc2nccc(C(O)C[C@H]3CC[C@@H](CC3)NCc3ccc4OCCOc4c3)c2c1 KXTMYJBJTDOVIC-NUDRXGSASA-N 0.000 claims 1
• HCLNGONVVJJJSF-UHFFFAOYSA-N N-(6-methoxyquinolin-4-yl)cyclohexanecarboxamide Chemical compound COC1=CC=C2N=CC=C(NC(=O)C3CCCCC3)C2=C1 HCLNGONVVJJJSF-UHFFFAOYSA-N 0.000 claims 1
• WYUMOJZSXWEIPU-WKILWMFISA-N N1=C2SC=NC2=CC(CN[C@H]2CC[C@@H](CC2)C(=O)NC2=CC=NC3=CC=C(N=C32)OC)=C1 Chemical compound N1=C2SC=NC2=CC(CN[C@H]2CC[C@@H](CC2)C(=O)NC2=CC=NC3=CC=C(N=C32)OC)=C1 WYUMOJZSXWEIPU-WKILWMFISA-N 0.000 claims 1
• GINYYMFAGWWUOX-SHTZXODSSA-N N1=C2SN=NC2=CC(CN[C@H]2CC[C@@H](CC2)C(=O)NC2=CC=NC3=CC=C(N=C32)OC)=C1 Chemical compound N1=C2SN=NC2=CC(CN[C@H]2CC[C@@H](CC2)C(=O)NC2=CC=NC3=CC=C(N=C32)OC)=C1 GINYYMFAGWWUOX-SHTZXODSSA-N 0.000 claims 1
• LXMYTYOWYIYDRP-UHFFFAOYSA-N N1=CC=C(N)C2=NC(C)=CC=C21 Chemical compound N1=CC=C(N)C2=NC(C)=CC=C21 LXMYTYOWYIYDRP-UHFFFAOYSA-N 0.000 claims 1
• INPHYSUGIAWTBU-IYARVYRRSA-N O1CCOC2=CC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=C(F)C=C(C=C43)OC)=CC=C21 Chemical compound O1CCOC2=CC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=C(F)C=C(C=C43)OC)=CC=C21 INPHYSUGIAWTBU-IYARVYRRSA-N 0.000 claims 1
• WHNQBMVNTXFLDL-MXVIHJGJSA-N O1CCOC2=CC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=CC=C(N=C43)OCCCN)=CC=C21 Chemical compound O1CCOC2=CC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=CC=C(N=C43)OCCCN)=CC=C21 WHNQBMVNTXFLDL-MXVIHJGJSA-N 0.000 claims 1
• UHXALYJLYLDNOL-QAQDUYKDSA-N S1CC(=O)NC2=CC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 Chemical class S1CC(=O)NC2=CC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 UHXALYJLYLDNOL-QAQDUYKDSA-N 0.000 claims 1
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
• 150000001555 benzenes Chemical class 0.000 claims 1
• OSVVTVLREDJKKV-WGSAOQKQSA-N chembl1926762 Chemical compound O1CCOC2=CC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=CC=C(C=C43)OC)=CC=C21 OSVVTVLREDJKKV-WGSAOQKQSA-N 0.000 claims 1
• MXFMDXNMFBQMSA-IYARVYRRSA-N chembl1926764 Chemical compound O1CCOC2=CC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 MXFMDXNMFBQMSA-IYARVYRRSA-N 0.000 claims 1
• HVWFFJFLJLATFZ-WKILWMFISA-N chembl1926864 Chemical class O1CCOC(C=N2)=C1C=C2CN[C@H](CC1)CC[C@@H]1C(=O)NC1=CC=NC2=CC=C(OC)N=C21 HVWFFJFLJLATFZ-WKILWMFISA-N 0.000 claims 1
• PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 claims 1
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
• 125000000596 cyclohexenyl group Chemical class C1(=CCCCC1)* 0.000 abstract description 2
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 411
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 352
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 218
• 239000000203 mixture Substances 0.000 description 194
• 239000000243 solution Substances 0.000 description 157
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 134
• 150000001412 amines Chemical class 0.000 description 111
• 239000007787 solid Substances 0.000 description 111
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 98
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 90
• 150000002500 ions Chemical class 0.000 description 89
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 87
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 82
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 76
• 235000019439 ethyl acetate Nutrition 0.000 description 76
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 75
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
• 238000006243 chemical reaction Methods 0.000 description 71
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 69
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 54
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 54
• 235000019441 ethanol Nutrition 0.000 description 53
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 52
• 239000000047 product Substances 0.000 description 52
• 239000000741 silica gel Substances 0.000 description 52
• 229910002027 silica gel Inorganic materials 0.000 description 52
• 150000002148 esters Chemical class 0.000 description 51
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 50
• 239000002904 solvent Substances 0.000 description 49
• 239000012458 free base Substances 0.000 description 47
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• WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
• 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
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• FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
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