JP2006522812A - 複素環ｍｃｈｒ１アンタゴニスト - Google Patents

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Publication number

JP2006522812A

JP2006522812A JP2006509727A JP2006509727A JP2006522812A JP 2006522812 A JP2006522812 A JP 2006522812A JP 2006509727 A JP2006509727 A JP 2006509727A JP 2006509727 A JP2006509727 A JP 2006509727A JP 2006522812 A JP2006522812 A JP 2006522812A

Authority

JP

Japan

Prior art keywords

methyl

compound

mmol

group

formula

Prior art date

2003-04-11

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Pending

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• 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 43
• 239000005557 antagonist Substances 0.000 title abstract description 10
• 101000581402 Homo sapiens Melanin-concentrating hormone receptor 1 Proteins 0.000 title description 8
• 102100027375 Melanin-concentrating hormone receptor 1 Human genes 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 341
• 238000000034 method Methods 0.000 claims abstract description 86
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
• 239000003814 drug Substances 0.000 claims abstract description 13
• -1 C 1 -C 3 alkyl Chemical group 0.000 claims description 210
• 238000006243 chemical reaction Methods 0.000 claims description 103
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 65
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 64
• 229910052757 nitrogen Inorganic materials 0.000 claims description 62
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 61
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 57
• 229910052739 hydrogen Inorganic materials 0.000 claims description 50
• 239000001257 hydrogen Substances 0.000 claims description 49
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 48
• 125000005843 halogen group Chemical group 0.000 claims description 46
• 125000000217 alkyl group Chemical group 0.000 claims description 44
• 239000002904 solvent Substances 0.000 claims description 44
• 150000003839 salts Chemical class 0.000 claims description 40
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
• 125000003118 aryl group Chemical group 0.000 claims description 37
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
• 125000001424 substituent group Chemical group 0.000 claims description 36
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 28
• 150000002431 hydrogen Chemical class 0.000 claims description 25
• 229910052763 palladium Inorganic materials 0.000 claims description 24
• 229910052717 sulfur Inorganic materials 0.000 claims description 24
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
• 229910052799 carbon Inorganic materials 0.000 claims description 20
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
• 125000001072 heteroaryl group Chemical group 0.000 claims description 19
• 125000004043 oxo group Chemical group O=* 0.000 claims description 19
• 229910052760 oxygen Inorganic materials 0.000 claims description 19
• 125000003545 alkoxy group Chemical group 0.000 claims description 18
• 125000003282 alkyl amino group Chemical group 0.000 claims description 18
• 208000008589 Obesity Diseases 0.000 claims description 17
• 150000001412 amines Chemical class 0.000 claims description 17
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 17
• 235000020824 obesity Nutrition 0.000 claims description 17
• 239000012453 solvate Substances 0.000 claims description 16
• 241000124008 Mammalia Species 0.000 claims description 15
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 15
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 14
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 14
• 125000004414 alkyl thio group Chemical group 0.000 claims description 12
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 11
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 10
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 10
• 206010012601 diabetes mellitus Diseases 0.000 claims description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 125000002619 bicyclic group Chemical group 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• 208000019901 Anxiety disease Diseases 0.000 claims description 7
• 230000036506 anxiety Effects 0.000 claims description 7
• 239000003795 chemical substances by application Substances 0.000 claims description 7
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 7
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 6
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 6
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 6
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
• 239000003054 catalyst Substances 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
• 239000011593 sulfur Substances 0.000 claims description 5
• YMDKGGMAMAEFNG-UHFFFAOYSA-N 6-(4-chlorophenyl)-3-[2-(dimethylamino)-3-methylbenzimidazol-5-yl]thieno[3,2-d]pyrimidin-4-one Chemical compound C1=C2N(C)C(N(C)C)=NC2=CC=C1N(C(C=1S2)=O)C=NC=1C=C2C1=CC=C(Cl)C=C1 YMDKGGMAMAEFNG-UHFFFAOYSA-N 0.000 claims description 4
• UODVREUPOUDRNR-UHFFFAOYSA-N 6-(4-chlorophenyl)-3-[6-(pyrrolidin-1-ylmethyl)naphthalen-2-yl]thieno[3,2-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1C(S1)=CC2=C1C(=O)N(C=1C=C3C=CC(CN4CCCC4)=CC3=CC=1)C=N2 UODVREUPOUDRNR-UHFFFAOYSA-N 0.000 claims description 4
• HTLJHDQWVDIZCQ-UHFFFAOYSA-N 6-(4-chlorophenyl)-3-[6-[(4-hydroxypiperidin-1-yl)methyl]naphthalen-2-yl]thieno[3,2-d]pyrimidin-4-one Chemical compound C1CC(O)CCN1CC1=CC=C(C=C(C=C2)N3C(C=4SC(=CC=4N=C3)C=3C=CC(Cl)=CC=3)=O)C2=C1 HTLJHDQWVDIZCQ-UHFFFAOYSA-N 0.000 claims description 4
• 239000000556 agonist Substances 0.000 claims description 4
• 229910052786 argon Inorganic materials 0.000 claims description 4
• 239000003153 chemical reaction reagent Substances 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 125000001153 fluoro group Chemical group F* 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000003367 polycyclic group Chemical group 0.000 claims description 4
• 229910052727 yttrium Inorganic materials 0.000 claims description 4
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
• XYCZXPVVNCEPEF-UHFFFAOYSA-N 6-(4-chlorophenyl)-3-[2-[(4-methylpiperazin-1-yl)methyl]-1-benzothiophen-5-yl]thieno[3,2-d]pyrimidin-4-one Chemical compound C1CN(C)CCN1CC1=CC2=CC(N3C(C=4SC(=CC=4N=C3)C=3C=CC(Cl)=CC=3)=O)=CC=C2S1 XYCZXPVVNCEPEF-UHFFFAOYSA-N 0.000 claims description 3
• ATILBCJMFACSLA-UHFFFAOYSA-N 6-phenyl-3-[2-(pyrrolidin-1-ylmethyl)quinolin-6-yl]thieno[3,2-d]pyrimidin-4-one Chemical compound S1C=2C(=O)N(C=3C=C4C=CC(CN5CCCC5)=NC4=CC=3)C=NC=2C=C1C1=CC=CC=C1 ATILBCJMFACSLA-UHFFFAOYSA-N 0.000 claims description 3
• 206010003210 Arteriosclerosis Diseases 0.000 claims description 3
• 206010020772 Hypertension Diseases 0.000 claims description 3
• 150000001413 amino acids Chemical class 0.000 claims description 3
• 208000011775 arteriosclerosis disease Diseases 0.000 claims description 3
• 239000003638 chemical reducing agent Substances 0.000 claims description 3
• 125000001475 halogen functional group Chemical group 0.000 claims description 3
• 238000010438 heat treatment Methods 0.000 claims description 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
• JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 3
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
• FDIBWJRZRJTTOK-UHFFFAOYSA-N 6-(4-chlorophenyl)-3-[2-[(2-methyl-4,5-dihydroimidazol-1-yl)methyl]quinolin-6-yl]thieno[3,2-d]pyrimidin-4-one Chemical compound CC1=NCCN1CC1=CC=C(C=C(C=C2)N3C(C=4SC(=CC=4N=C3)C=3C=CC(Cl)=CC=3)=O)C2=N1 FDIBWJRZRJTTOK-UHFFFAOYSA-N 0.000 claims description 2
• SANXLPAIECKXLI-UHFFFAOYSA-N 6-(4-fluorophenyl)-3-[2-(piperidin-1-ylmethyl)quinolin-6-yl]thieno[3,2-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1C(S1)=CC2=C1C(=O)N(C=1C=C3C=CC(CN4CCCCC4)=NC3=CC=1)C=N2 SANXLPAIECKXLI-UHFFFAOYSA-N 0.000 claims description 2
• 229940124802 CB1 antagonist Drugs 0.000 claims description 2
• 108010016122 Ghrelin Receptors Proteins 0.000 claims description 2
• 102100039256 Growth hormone secretagogue receptor type 1 Human genes 0.000 claims description 2
• 101000993364 Homo sapiens Ciliary neurotrophic factor Proteins 0.000 claims description 2
• 101000978418 Homo sapiens Melanocortin receptor 4 Proteins 0.000 claims description 2
• 229940086609 Lipase inhibitor Drugs 0.000 claims description 2
• 102100023724 Melanocortin receptor 4 Human genes 0.000 claims description 2
• 239000007868 Raney catalyst Substances 0.000 claims description 2
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
• 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
• 238000006619 Stille reaction Methods 0.000 claims description 2
• 238000006069 Suzuki reaction reaction Methods 0.000 claims description 2
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 2
• 150000002148 esters Chemical class 0.000 claims description 2
• 239000003112 inhibitor Substances 0.000 claims description 2
• 229940125425 inverse agonist Drugs 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 230000001561 neurotransmitter reuptake Effects 0.000 claims description 2
• 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 2
• 239000000018 receptor agonist Substances 0.000 claims description 2
• 229940044601 receptor agonist Drugs 0.000 claims description 2
• 229940044551 receptor antagonist Drugs 0.000 claims description 2
• 239000002464 receptor antagonist Substances 0.000 claims description 2
• WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 claims description 2
• 238000006467 substitution reaction Methods 0.000 claims description 2
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
• LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims 4
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical group C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 2
• OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 2
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 2
• LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims 2
• HJFIRBMYMDXWII-UHFFFAOYSA-N 6-(4-fluorophenyl)-3-[2-(pyrrolidin-1-ylmethyl)quinolin-6-yl]thieno[3,2-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1C(S1)=CC2=C1C(=O)N(C=1C=C3C=CC(CN4CCCC4)=NC3=CC=1)C=N2 HJFIRBMYMDXWII-UHFFFAOYSA-N 0.000 claims 1
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
• 239000002168 alkylating agent Substances 0.000 claims 1
• 229940100198 alkylating agent Drugs 0.000 claims 1
• 230000002152 alkylating effect Effects 0.000 claims 1
• 239000013626 chemical specie Substances 0.000 claims 1
• 239000007822 coupling agent Substances 0.000 claims 1
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
• 238000002360 preparation method Methods 0.000 abstract description 5
• 108091008039 hormone receptors Proteins 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 363
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 230
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 182
• 239000000203 mixture Substances 0.000 description 180
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 167
• 239000007787 solid Substances 0.000 description 145
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 109
• 239000000243 solution Substances 0.000 description 101
• 239000000460 chlorine Substances 0.000 description 97
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 86
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 74
• 239000000543 intermediate Substances 0.000 description 72
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 69
• 235000019439 ethyl acetate Nutrition 0.000 description 66
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 57
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
• 238000002474 experimental method Methods 0.000 description 48
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 46
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 42
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
• 239000000047 product Substances 0.000 description 40
• 239000011541 reaction mixture Substances 0.000 description 39
• 239000000741 silica gel Substances 0.000 description 38
• 229910002027 silica gel Inorganic materials 0.000 description 38
• 235000002639 sodium chloride Nutrition 0.000 description 37
• 238000010992 reflux Methods 0.000 description 34
• 239000002244 precipitate Substances 0.000 description 32
• 238000010898 silica gel chromatography Methods 0.000 description 30
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
• 239000000706 filtrate Substances 0.000 description 27
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 26
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 22
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 22
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 21
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-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
• 230000002829 reductive effect Effects 0.000 description 20
• 235000019441 ethanol Nutrition 0.000 description 18
• 239000012044 organic layer Substances 0.000 description 18
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
• 239000003921 oil Substances 0.000 description 17
• 235000019198 oils Nutrition 0.000 description 16
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 238000002953 preparative HPLC Methods 0.000 description 15
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
• 229910021529 ammonia Inorganic materials 0.000 description 13
• 239000012267 brine Substances 0.000 description 13
• 239000000843 powder Substances 0.000 description 13
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
• 238000004440 column chromatography Methods 0.000 description 12
• 239000012043 crude product Substances 0.000 description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 11
• 235000019253 formic acid Nutrition 0.000 description 11
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
• ALWFLYMKFZJTBB-RQZCQDPDSA-N CN(C)/C=N/C1=C(C(=O)OC)SC(C=2C=CC(Cl)=CC=2)=C1 Chemical compound CN(C)/C=N/C1=C(C(=O)OC)SC(C=2C=CC(Cl)=CC=2)=C1 ALWFLYMKFZJTBB-RQZCQDPDSA-N 0.000 description 10
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
• 239000002253 acid Substances 0.000 description 10
• 238000004587 chromatography analysis Methods 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 9
• 238000003818 flash chromatography Methods 0.000 description 9
• 238000009472 formulation Methods 0.000 description 9
• 239000002609 medium Substances 0.000 description 9
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 9
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 8
• 0 CC(C)(C=C(C=C1)NC)C=C1N(C(*)=NC(I)=C1*)C1=O Chemical compound CC(C)(C=C(C=C1)NC)C=C1N(C(*)=NC(I)=C1*)C1=O 0.000 description 8
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