BRPI0710182A2 - compostos orgÂnicos. - Google Patents

Info

Publication number

BRPI0710182A2

BRPI0710182A2 BRPI0710182-1A BRPI0710182A BRPI0710182A2 BR PI0710182 A2 BRPI0710182 A2 BR PI0710182A2 BR PI0710182 A BRPI0710182 A BR PI0710182A BR PI0710182 A2 BRPI0710182 A2 BR PI0710182A2

Authority

BR

Brazil

Prior art keywords

substituted

unsubstituted

hydroxy

thiadiazolidin

phenyl

Prior art date

2006-03-31

Links

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• 150000002894 organic compounds Chemical class 0.000 title abstract description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 489
• 230000000694 effects Effects 0.000 claims abstract description 31
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 26
• 102000002727 Protein Tyrosine Phosphatase Human genes 0.000 claims abstract description 23
• 108020000494 protein-tyrosine phosphatase Proteins 0.000 claims abstract description 23
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 18
• 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
• 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 16
• 208000017170 Lipid metabolism disease Diseases 0.000 claims abstract description 16
• 230000001404 mediated effect Effects 0.000 claims abstract description 15
• 208000023178 Musculoskeletal disease Diseases 0.000 claims abstract description 14
• 206010020772 Hypertension Diseases 0.000 claims abstract description 12
• 208000008589 Obesity Diseases 0.000 claims abstract description 12
• 235000020824 obesity Nutrition 0.000 claims abstract description 12
• 208000002705 Glucose Intolerance Diseases 0.000 claims abstract description 11
• 206010018429 Glucose tolerance impaired Diseases 0.000 claims abstract description 11
• 206010061218 Inflammation Diseases 0.000 claims abstract description 11
• 208000001132 Osteoporosis Diseases 0.000 claims abstract description 11
• 206010033645 Pancreatitis Diseases 0.000 claims abstract description 11
• 210000004204 blood vessel Anatomy 0.000 claims abstract description 11
• 201000011510 cancer Diseases 0.000 claims abstract description 11
• 210000000987 immune system Anatomy 0.000 claims abstract description 11
• 230000004054 inflammatory process Effects 0.000 claims abstract description 11
• 208000002551 irritable bowel syndrome Diseases 0.000 claims abstract description 11
• 230000002792 vascular Effects 0.000 claims abstract description 11
• 208000023589 ischemic disease Diseases 0.000 claims abstract description 10
• 230000000626 neurodegenerative effect Effects 0.000 claims abstract description 10
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 9
• 201000010099 disease Diseases 0.000 claims abstract description 9
• 208000037803 restenosis Diseases 0.000 claims abstract description 7
• -1 - S (O) -OH Chemical group 0.000 claims description 298
• 125000000217 alkyl group Chemical group 0.000 claims description 169
• 150000003839 salts Chemical class 0.000 claims description 126
• 125000000623 heterocyclic group Chemical group 0.000 claims description 103
• 125000003118 aryl group Chemical group 0.000 claims description 101
• 239000001257 hydrogen Substances 0.000 claims description 101
• 229910052739 hydrogen Inorganic materials 0.000 claims description 101
• 238000000034 method Methods 0.000 claims description 94
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
• 125000001072 heteroaryl group Chemical group 0.000 claims description 62
• 150000002431 hydrogen Chemical class 0.000 claims description 61
• 125000003545 alkoxy group Chemical group 0.000 claims description 60
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 54
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 50
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 50
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
• 239000002253 acid Substances 0.000 claims description 43
• 229910052736 halogen Inorganic materials 0.000 claims description 42
• 150000002367 halogens Chemical group 0.000 claims description 42
• 125000001424 substituent group Chemical group 0.000 claims description 42
• 229910052799 carbon Inorganic materials 0.000 claims description 41
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 38
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 35
• 150000001721 carbon Chemical group 0.000 claims description 35
• 125000002947 alkylene group Chemical group 0.000 claims description 34
• 125000004104 aryloxy group Chemical group 0.000 claims description 32
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 30
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
• 125000004414 alkyl thio group Chemical group 0.000 claims description 27
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims description 25
• 125000002252 acyl group Chemical group 0.000 claims description 24
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
• 125000001589 carboacyl group Chemical group 0.000 claims description 23
• 125000005110 aryl thio group Chemical group 0.000 claims description 22
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 22
• 125000004423 acyloxy group Chemical group 0.000 claims description 20
• 229910052760 oxygen Inorganic materials 0.000 claims description 20
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
• 239000001301 oxygen Substances 0.000 claims description 18
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 17
• 101710128896 Tyrosine-protein phosphatase non-receptor type 1 Proteins 0.000 claims description 16
• 102100033001 Tyrosine-protein phosphatase non-receptor type 1 Human genes 0.000 claims description 16
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 16
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 14
• 125000003282 alkyl amino group Chemical group 0.000 claims description 14
• 239000003814 drug Substances 0.000 claims description 13
• 241000124008 Mammalia Species 0.000 claims description 12
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
• 229940080818 propionamide Drugs 0.000 claims description 11
• GLZXFITXXAMCRJ-UHFFFAOYSA-N azepin-4-one Chemical compound O=C1C=CC=NC=C1 GLZXFITXXAMCRJ-UHFFFAOYSA-N 0.000 claims description 10
• 239000000883 anti-obesity agent Substances 0.000 claims description 9
• 229940125710 antiobesity agent Drugs 0.000 claims description 9
• 150000004702 methyl esters Chemical class 0.000 claims description 9
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 7
• 239000003472 antidiabetic agent Substances 0.000 claims description 7
• 229940030600 antihypertensive agent Drugs 0.000 claims description 7
• 239000002220 antihypertensive agent Substances 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 7
• 238000002360 preparation method Methods 0.000 claims description 7
• 208000035473 Communicable disease Diseases 0.000 claims description 6
• 150000001412 amines Chemical class 0.000 claims description 6
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 6
• 239000008103 glucose Substances 0.000 claims description 6
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
• 229940124530 sulfonamide Drugs 0.000 claims description 6
• 229940125708 antidiabetic agent Drugs 0.000 claims description 5
• 239000003524 antilipemic agent Substances 0.000 claims description 5
• 150000002148 esters Chemical class 0.000 claims description 5
• 125000004470 heterocyclooxy group Chemical group 0.000 claims description 5
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 5
• JSZAZZQHDRHICK-UHFFFAOYSA-N 1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound O=C1CNS(=O)(=O)N1 JSZAZZQHDRHICK-UHFFFAOYSA-N 0.000 claims description 4
• 239000005711 Benzoic acid Substances 0.000 claims description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• VAMZMKAHERCOQK-UHFFFAOYSA-N 5-[4-(3-aminopropyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC(CCCN)=CC=C1N1S(=O)(=O)NC(=O)C1 VAMZMKAHERCOQK-UHFFFAOYSA-N 0.000 claims description 3
• 150000003863 ammonium salts Chemical class 0.000 claims description 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
• 229940047889 isobutyramide Drugs 0.000 claims description 3
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
• MEOZFUYXLCDYGA-UHFFFAOYSA-N azepane-1-carboxylic acid Chemical compound OC(=O)N1CCCCCC1 MEOZFUYXLCDYGA-UHFFFAOYSA-N 0.000 claims description 2
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
• 230000002401 inhibitory effect Effects 0.000 claims description 2
• YCSBCCARSNJISH-UHFFFAOYSA-N n-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]methanesulfonamide Chemical compound OC1=CC(CCNS(=O)(=O)C)=CC=C1N1S(=O)(=O)NC(=O)C1 YCSBCCARSNJISH-UHFFFAOYSA-N 0.000 claims description 2
• UYVRHHKJWRAZDW-UHFFFAOYSA-N n-[4-(3-hydroxy-2-methylphenoxy)butyl]-3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanamide Chemical compound CC1=C(O)C=CC=C1OCCCCNC(=O)CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 UYVRHHKJWRAZDW-UHFFFAOYSA-N 0.000 claims description 2
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 4
• 125000004463 2,4-dimethyl-thiazol-5-yl group Chemical group CC=1SC(=C(N1)C)* 0.000 claims 1
• JOUMBESLECZHQX-UHFFFAOYSA-N 2-hydroxy-6-[4-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanoylamino]butoxy]benzoic acid Chemical compound OC(=O)C1=C(O)C=CC=C1OCCCCNC(=O)CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 JOUMBESLECZHQX-UHFFFAOYSA-N 0.000 claims 1
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
• 125000004429 atom Chemical group 0.000 claims 1
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
• ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 claims 1
• 125000004404 heteroalkyl group Chemical group 0.000 claims 1
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 1
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
• KMSVUPAFIVOGEC-FUHWJXTLSA-N n-[(1r,2s)-2-[[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]methyl]cyclohexyl]benzenesulfonamide Chemical compound N([C@@H]1CCCC[C@H]1CC=1C=C(C(=CC=1)N1S(NC(=O)C1)(=O)=O)O)S(=O)(=O)C1=CC=CC=C1 KMSVUPAFIVOGEC-FUHWJXTLSA-N 0.000 claims 1
• BRMGTUAFMILQLR-OLZOCXBDSA-N n-[(1s,2r)-2-[[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]methyl]cyclohexyl]methanesulfonamide Chemical compound CS(=O)(=O)N[C@H]1CCCC[C@@H]1CC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 BRMGTUAFMILQLR-OLZOCXBDSA-N 0.000 claims 1
• JERNCWVDXCVZEU-UHFFFAOYSA-N n-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]benzenesulfonamide Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCNS(=O)(=O)C1=CC=CC=C1 JERNCWVDXCVZEU-UHFFFAOYSA-N 0.000 claims 1
• UWAJPYAPFJCQTI-UHFFFAOYSA-N n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]-1-phenylmethanesulfonamide Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCCNS(=O)(=O)CC1=CC=CC=C1 UWAJPYAPFJCQTI-UHFFFAOYSA-N 0.000 claims 1
• XSAXZNVHWVQTLU-UHFFFAOYSA-N n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]-2,5-bis(2,2,2-trifluoroethoxy)benzenesulfonamide Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCCNS(=O)(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F XSAXZNVHWVQTLU-UHFFFAOYSA-N 0.000 claims 1
• UIZQNIZUACDTPY-UHFFFAOYSA-N n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]-3,4-dimethoxybenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NCCCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 UIZQNIZUACDTPY-UHFFFAOYSA-N 0.000 claims 1
• CCFNBOVNMOLCHA-UHFFFAOYSA-N n-[4-(2-acetyl-3-hydroxyphenoxy)butyl]-3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanamide Chemical compound CC(=O)C1=C(O)C=CC=C1OCCCCNC(=O)CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 CCFNBOVNMOLCHA-UHFFFAOYSA-N 0.000 claims 1
• 230000004770 neurodegeneration Effects 0.000 claims 1
• HNDXKIMMSFCCFW-UHFFFAOYSA-N propane-2-sulphonic acid Chemical compound CC(C)S(O)(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-N 0.000 claims 1
• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
• 239000003112 inhibitor Substances 0.000 abstract description 19
• 206010012601 diabetes mellitus Diseases 0.000 abstract description 9
• 208000035475 disorder Diseases 0.000 abstract description 7
• 208000006575 hypertriglyceridemia Diseases 0.000 abstract description 7
• 201000009030 Carcinoma Diseases 0.000 abstract description 6
• 208000031226 Hyperlipidaemia Diseases 0.000 abstract description 6
• 210000001789 adipocyte Anatomy 0.000 abstract description 6
• 102000004190 Enzymes Human genes 0.000 abstract description 5
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• 208000015181 infectious disease Diseases 0.000 abstract description 5
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• 206010024627 liposarcoma Diseases 0.000 abstract description 5
• 230000027455 binding Effects 0.000 abstract description 4
• 102000014400 SH2 domains Human genes 0.000 abstract 1
• 108050003452 SH2 domains Proteins 0.000 abstract 1
• DCWXELXMIBXGTH-UHFFFAOYSA-N phosphotyrosine Chemical compound OC(=O)C(N)CC1=CC=C(OP(O)(O)=O)C=C1 DCWXELXMIBXGTH-UHFFFAOYSA-N 0.000 abstract 1
• 230000002265 prevention Effects 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 259
• 239000000243 solution Substances 0.000 description 217
• 239000000203 mixture Substances 0.000 description 208
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 139
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 133
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 132
• 239000002904 solvent Substances 0.000 description 127
• 235000019439 ethyl acetate Nutrition 0.000 description 126
• 230000002829 reductive effect Effects 0.000 description 125
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 103
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 89
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 79
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 70
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 66
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 65
• 239000012267 brine Substances 0.000 description 64
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
• 239000007787 solid Substances 0.000 description 50
• 239000012074 organic phase Substances 0.000 description 46
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 45
• 238000006243 chemical reaction Methods 0.000 description 41
• 238000003818 flash chromatography Methods 0.000 description 41
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 40
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• 235000019341 magnesium sulphate Nutrition 0.000 description 35
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 33
• 239000003921 oil Substances 0.000 description 32
• 235000019198 oils Nutrition 0.000 description 32
• 239000012044 organic layer Substances 0.000 description 32
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• 238000005481 NMR spectroscopy Methods 0.000 description 29
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
• 239000003480 eluent Substances 0.000 description 28
• 229910052938 sodium sulfate Inorganic materials 0.000 description 28
• 235000011152 sodium sulphate Nutrition 0.000 description 28
• 238000004128 high performance liquid chromatography Methods 0.000 description 27
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 27
• 230000014759 maintenance of location Effects 0.000 description 26
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
• 239000003054 catalyst Substances 0.000 description 25
• 239000000460 chlorine Chemical group 0.000 description 25
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
• 239000000725 suspension Substances 0.000 description 23
• 229920002554 vinyl polymer Polymers 0.000 description 22
• 239000000706 filtrate Substances 0.000 description 21
• 239000011780 sodium chloride Substances 0.000 description 20
• 239000002585 base Substances 0.000 description 19
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 18
• 238000003756 stirring Methods 0.000 description 16
• UMPCRQWRRIQOMZ-UHFFFAOYSA-N 5-(4-iodo-2-phenylmethoxyphenyl)-1,1-dioxo-2-(2-trimethylsilylethyl)-1,2,5-thiadiazolidin-3-one Chemical compound O=S1(=O)N(CC[Si](C)(C)C)C(=O)CN1C1=CC=C(I)C=C1OCC1=CC=CC=C1 UMPCRQWRRIQOMZ-UHFFFAOYSA-N 0.000 description 15
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 15
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 14
• 229910052763 palladium Inorganic materials 0.000 description 14
• 229920006395 saturated elastomer Polymers 0.000 description 14
• 239000007858 starting material Substances 0.000 description 14
• 238000005160 1H NMR spectroscopy Methods 0.000 description 12
• CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 12
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
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