RU2251419C2 - Производные бензотиазола - Google Patents

Info

Publication number

RU2251419C2

RU2251419C2 RU2003100518/15A RU2003100518A RU2251419C2 RU 2251419 C2 RU2251419 C2 RU 2251419C2 RU 2003100518/15 A RU2003100518/15 A RU 2003100518/15A RU 2003100518 A RU2003100518 A RU 2003100518A RU 2251419 C2 RU2251419 C2 RU 2251419C2

Authority

RU

Russia

Prior art keywords

methoxy

ylbenzothiazol

morpholin

alkyl

benzamide

Prior art date

2000-06-21

Links

• Espacenet
• Global Dossier
• Discuss

• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title claims abstract description 4
• 239000003814 drug Substances 0.000 claims abstract description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
• 201000010099 disease Diseases 0.000 claims abstract description 4
• 230000001404 mediated effect Effects 0.000 claims abstract description 4
• 150000001875 compounds Chemical class 0.000 claims description 411
• -1 2,3-dihydro-1H-indolyl Chemical group 0.000 claims description 243
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 104
• 125000000217 alkyl group Chemical group 0.000 claims description 84
• DOIKFFGWUPLXGA-UHFFFAOYSA-N 4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-amine Chemical compound C1=2SC(N)=NC=2C(OC)=CC=C1N1CCOCC1 DOIKFFGWUPLXGA-UHFFFAOYSA-N 0.000 claims description 62
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 56
• OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 44
• 125000003545 alkoxy group Chemical group 0.000 claims description 30
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 29
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 29
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims description 25
• 125000003118 aryl group Chemical group 0.000 claims description 24
• 229910052736 halogen Inorganic materials 0.000 claims description 23
• 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 22
• 229960005305 adenosine Drugs 0.000 claims description 22
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 20
• 150000002367 halogens Chemical class 0.000 claims description 17
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 125000005605 benzo group Chemical group 0.000 claims description 6
• 125000000623 heterocyclic group Chemical group 0.000 claims description 6
• 125000002757 morpholinyl group Chemical group 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 125000004193 piperazinyl group Chemical group 0.000 claims description 6
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 5
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
• VEHWZDFLDCERBM-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-4-(methylaminomethyl)benzamide Chemical compound C1=CC(CNC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 VEHWZDFLDCERBM-UHFFFAOYSA-N 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• HHJKIHFTQXMIDY-UHFFFAOYSA-N COC1=CC=C(C2=C1N=C(S2)C1N(CCOC1)C(=O)N)C1=CC=CC=C1 Chemical compound COC1=CC=C(C2=C1N=C(S2)C1N(CCOC1)C(=O)N)C1=CC=CC=C1 HHJKIHFTQXMIDY-UHFFFAOYSA-N 0.000 claims description 4
• NLMRREJKPGGHBJ-UHFFFAOYSA-N COC1=CC=C(C2=C1N=C(S2)C2=C(SC(=C2)C)C(=O)N)C2=CC(=NC=C2)C Chemical compound COC1=CC=C(C2=C1N=C(S2)C2=C(SC(=C2)C)C(=O)N)C2=CC(=NC=C2)C NLMRREJKPGGHBJ-UHFFFAOYSA-N 0.000 claims description 4
• IMJLUKIDNDTQKQ-UHFFFAOYSA-N NC=1C=C(C=CC1)C1=CC=C(C=2N=C(SC21)C2=C(SC(=C2)C)C(=O)N)OC Chemical compound NC=1C=C(C=CC1)C1=CC=C(C=2N=C(SC21)C2=C(SC(=C2)C)C(=O)N)OC IMJLUKIDNDTQKQ-UHFFFAOYSA-N 0.000 claims description 4
• 150000002431 hydrogen Chemical class 0.000 claims description 4
• KEJUVOFMRNLHJQ-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 KEJUVOFMRNLHJQ-UHFFFAOYSA-N 0.000 claims description 4
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 4
• SKXVYZIWQHIZQQ-UHFFFAOYSA-N tert-butyl 4-[(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)carbamoyl]piperidine-1-carboxylate Chemical compound C1=2SC(NC(=O)C3CCN(CC3)C(=O)OC(C)(C)C)=NC=2C(OC)=CC=C1N1CCOCC1 SKXVYZIWQHIZQQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
• CEKSPMMCISUSTR-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7-octahydroquinoline Chemical compound C1CCC2CCCNC2=C1 CEKSPMMCISUSTR-UHFFFAOYSA-N 0.000 claims description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• QWMBZRZDPAXYTF-UHFFFAOYSA-N 4-(hydroxymethyl)-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CO)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 QWMBZRZDPAXYTF-UHFFFAOYSA-N 0.000 claims description 3
• WUSOYFYKFSTOJR-UHFFFAOYSA-N 4-chloro-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-3-(pyrrolidin-1-ylmethyl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=C(CN4CCCC4)C(Cl)=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 WUSOYFYKFSTOJR-UHFFFAOYSA-N 0.000 claims description 3
• TUWCLXQQGOTDDG-UHFFFAOYSA-N COC1=CC=C(C2=C1N=C(S2)C2=C(OC(=C2)C)C(=O)N)C2=CC=CC=C2 Chemical compound COC1=CC=C(C2=C1N=C(S2)C2=C(OC(=C2)C)C(=O)N)C2=CC=CC=C2 TUWCLXQQGOTDDG-UHFFFAOYSA-N 0.000 claims description 3
• VKRAIIVFAQKSKY-UHFFFAOYSA-N COC1=CC=C(C2=C1N=C(S2)C2=C(SC(=C2)C)C(=O)N)C2=CC=CC=C2 Chemical compound COC1=CC=C(C2=C1N=C(S2)C2=C(SC(=C2)C)C(=O)N)C2=CC=CC=C2 VKRAIIVFAQKSKY-UHFFFAOYSA-N 0.000 claims description 3
• QPWGCRDJQLEZRJ-UHFFFAOYSA-N COC1=CC=C(C2=C1N=C(S2)C2=C(SC(=C2)C)C(=O)N)C2=CC=NC=C2 Chemical compound COC1=CC=C(C2=C1N=C(S2)C2=C(SC(=C2)C)C(=O)N)C2=CC=NC=C2 QPWGCRDJQLEZRJ-UHFFFAOYSA-N 0.000 claims description 3
• UKGVUXYVQUENLH-UHFFFAOYSA-N COC1=CC=C(C2=C1N=C(S2)C2=C(SC(=C2)C)C(=O)N)C=2C=NC=CC2 Chemical compound COC1=CC=C(C2=C1N=C(S2)C2=C(SC(=C2)C)C(=O)N)C=2C=NC=CC2 UKGVUXYVQUENLH-UHFFFAOYSA-N 0.000 claims description 3
• AZSGDNXZNRSTER-UHFFFAOYSA-N COC1=CC=C(C2=C1N=C(S2)C2N(CCC(C2)C(=O)N)C(C)=O)N2CCOCC2 Chemical compound COC1=CC=C(C2=C1N=C(S2)C2N(CCC(C2)C(=O)N)C(C)=O)N2CCOCC2 AZSGDNXZNRSTER-UHFFFAOYSA-N 0.000 claims description 3
• SLFFYIOTDHJEQL-UHFFFAOYSA-N COC1=CC=C(C2=C1N=C(S2)C2N(CCOC2)C(=O)N)C=2N=C(SC2)C=2C=NC(=CC2)C Chemical compound COC1=CC=C(C2=C1N=C(S2)C2N(CCOC2)C(=O)N)C=2N=C(SC2)C=2C=NC(=CC2)C SLFFYIOTDHJEQL-UHFFFAOYSA-N 0.000 claims description 3
• BJINHRAEXDZVBE-UHFFFAOYSA-N COC1=CC=C(C2=C1N=C(S2)C2N(CCOC2)C(=O)N)C=2N=C(SC2)N2CCN(CC2)C Chemical compound COC1=CC=C(C2=C1N=C(S2)C2N(CCOC2)C(=O)N)C=2N=C(SC2)N2CCN(CC2)C BJINHRAEXDZVBE-UHFFFAOYSA-N 0.000 claims description 3
• OBEVFBNWCFOHQJ-UHFFFAOYSA-N COC1=CC=C(C2=C1N=C(S2)C2N(CCS(C2)=O)C(=O)N)C2=CC=CC=C2 Chemical compound COC1=CC=C(C2=C1N=C(S2)C2N(CCS(C2)=O)C(=O)N)C2=CC=CC=C2 OBEVFBNWCFOHQJ-UHFFFAOYSA-N 0.000 claims description 3
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 3
• 125000004534 benzothien-2-yl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
• KLUQUYACYZVTAO-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-methylpyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(C)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 KLUQUYACYZVTAO-UHFFFAOYSA-N 0.000 claims description 3
• ANNVCGNKZBVUOC-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-3-(pyrrolidin-1-ylmethyl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=C(CN4CCCC4)C=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 ANNVCGNKZBVUOC-UHFFFAOYSA-N 0.000 claims description 3
• YYPCSESDMWDOFG-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-4-(trifluoromethyl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(=CC=3)C(F)(F)F)=NC=2C(OC)=CC=C1N1CCOCC1 YYPCSESDMWDOFG-UHFFFAOYSA-N 0.000 claims description 3
• GGPJGAFHQGWMQZ-UHFFFAOYSA-N n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=CN=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 GGPJGAFHQGWMQZ-UHFFFAOYSA-N 0.000 claims description 3
• HWDWQUMQAKXUAQ-UHFFFAOYSA-N n-(4-methoxy-7-thiophen-2-yl-1,3-benzothiazol-2-yl)-4-(pyrrolidin-1-ylmethyl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CN4CCCC4)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CS1 HWDWQUMQAKXUAQ-UHFFFAOYSA-N 0.000 claims description 3
• JYDYGXJAYSGYLW-UHFFFAOYSA-N n-[4-methoxy-7-(2-pyridin-2-yl-1,3-thiazol-4-yl)-1,3-benzothiazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(C)N=CC=3)=NC=2C(OC)=CC=C1C(N=1)=CSC=1C1=CC=CC=N1 JYDYGXJAYSGYLW-UHFFFAOYSA-N 0.000 claims description 3
• XILGMURDLOXRDG-UHFFFAOYSA-N n-[4-methoxy-7-(2-pyrrolidin-1-yl-1,3-thiazol-4-yl)-1,3-benzothiazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(C)N=CC=3)=NC=2C(OC)=CC=C1C(N=1)=CSC=1N1CCCC1 XILGMURDLOXRDG-UHFFFAOYSA-N 0.000 claims description 3
• SLUGOHJTLIVUJZ-UHFFFAOYSA-N n-[4-methoxy-7-[2-(4-methylpiperazin-1-yl)-1,3-thiazol-4-yl]-1,3-benzothiazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(C)N=CC=3)=NC=2C(OC)=CC=C1C(N=1)=CSC=1N1CCN(C)CC1 SLUGOHJTLIVUJZ-UHFFFAOYSA-N 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• 125000000335 thiazolyl group Chemical group 0.000 claims description 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
• 125000005869 (methoxyethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
• KPKNTUUIEVXMOH-UHFFFAOYSA-N 1,4-dioxa-8-azaspiro[4.5]decane Chemical compound O1CCOC11CCNCC1 KPKNTUUIEVXMOH-UHFFFAOYSA-N 0.000 claims description 2
• FOWOXWLATUAFNQ-UHFFFAOYSA-N 4-oxopiperidine-1-carboxylic acid Chemical compound OC(=O)N1CCC(=O)CC1 FOWOXWLATUAFNQ-UHFFFAOYSA-N 0.000 claims description 2
• PBZZYEBVYMPKJT-UHFFFAOYSA-N COC1=CC=C(C2=C1N=C(S2)C2N(CCS(C2)=O)C(=O)N)N2CCCCC2 Chemical compound COC1=CC=C(C2=C1N=C(S2)C2N(CCS(C2)=O)C(=O)N)N2CCCCC2 PBZZYEBVYMPKJT-UHFFFAOYSA-N 0.000 claims description 2
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• ZDBCPDBLXXFMOZ-UHFFFAOYSA-N n-(4-methoxy-1,3-benzothiazol-2-yl)benzamide Chemical compound N=1C=2C(OC)=CC=CC=2SC=1NC(=O)C1=CC=CC=C1 ZDBCPDBLXXFMOZ-UHFFFAOYSA-N 0.000 claims description 2
• LODRHLUBEKIPME-UHFFFAOYSA-N n-(4-methoxy-7-thiophen-2-yl-1,3-benzothiazol-2-yl)-2-methylpyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(C)N=CC=3)=NC=2C(OC)=CC=C1C1=CC=CS1 LODRHLUBEKIPME-UHFFFAOYSA-N 0.000 claims description 2
• VLBCWCSVPIXQMD-UHFFFAOYSA-N n-[4-methoxy-7-(2-pyridin-2-yl-1,3-thiazol-4-yl)-1,3-benzothiazol-2-yl]-4-(pyrrolidin-1-ylmethyl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CN4CCCC4)=CC=3)=NC=2C(OC)=CC=C1C(N=1)=CSC=1C1=CC=CC=N1 VLBCWCSVPIXQMD-UHFFFAOYSA-N 0.000 claims description 2
• PAQSHTQSRJVUNK-UHFFFAOYSA-N n-[4-methoxy-7-(5-methylthiophen-2-yl)-1,3-benzothiazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(C)N=CC=3)=NC=2C(OC)=CC=C1C1=CC=C(C)S1 PAQSHTQSRJVUNK-UHFFFAOYSA-N 0.000 claims description 2
• RICREVBYVNQMPF-UHFFFAOYSA-N n-[4-methoxy-7-[2-(6-methylpyridin-3-yl)-1,3-thiazol-4-yl]-1,3-benzothiazol-2-yl]-4-(pyrrolidin-1-ylmethyl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CN4CCCC4)=CC=3)=NC=2C(OC)=CC=C1C(N=1)=CSC=1C1=CC=C(C)N=C1 RICREVBYVNQMPF-UHFFFAOYSA-N 0.000 claims description 2
• JXWFTVZYGPPHPK-UHFFFAOYSA-N n-[7-(2-amino-1,3-thiazol-4-yl)-4-methoxy-1,3-benzothiazol-2-yl]-4-fluorobenzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(F)=CC=3)=NC=2C(OC)=CC=C1C1=CSC(N)=N1 JXWFTVZYGPPHPK-UHFFFAOYSA-N 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
• 150000004702 methyl esters Chemical class 0.000 claims 1
• 239000000546 pharmaceutical excipient Substances 0.000 claims 1
• 238000002360 preparation method Methods 0.000 abstract description 26
• 102000009346 Adenosine receptors Human genes 0.000 abstract description 13
• 108050000203 Adenosine receptors Proteins 0.000 abstract description 13
• 230000000694 effects Effects 0.000 abstract description 6
• 239000000126 substance Substances 0.000 abstract description 3
• 238000002560 therapeutic procedure Methods 0.000 abstract description 3
• 239000007787 solid Substances 0.000 description 344
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 155
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 144
• 239000000203 mixture Substances 0.000 description 83
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
• 238000000034 method Methods 0.000 description 67
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
• 239000000243 solution Substances 0.000 description 66
• 235000019439 ethyl acetate Nutrition 0.000 description 58
• 239000000047 product Substances 0.000 description 56
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
• 238000007429 general method Methods 0.000 description 55
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 54
• 239000000460 chlorine Substances 0.000 description 52
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
• 239000002904 solvent Substances 0.000 description 44
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
• 239000000741 silica gel Substances 0.000 description 31
• 229910002027 silica gel Inorganic materials 0.000 description 31
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
• 239000011541 reaction mixture Substances 0.000 description 29
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 27
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 27
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
• 238000003818 flash chromatography Methods 0.000 description 25
• 239000012074 organic phase Substances 0.000 description 25
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• 239000011734 sodium Substances 0.000 description 24
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