FI112488B - Aryylialkyyli- tai heteroaryylialkyylisubstituoidut pyrrolopyridatsiinijohdannaiset - Google Patents

Info

Publication number

FI112488B

FI112488B FI962892A FI962892A FI112488B FI 112488 B FI112488 B FI 112488B FI 962892 A FI962892 A FI 962892A FI 962892 A FI962892 A FI 962892A FI 112488 B FI112488 B FI 112488B

Authority

FI

Finland

Prior art keywords

group

pyridazine

pharmacologically acceptable

propenyl

fph

Prior art date

1994-01-19

Links

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• YTJAMOLQXDNLJC-UHFFFAOYSA-N N1N=CC=C2N=CC=C21 Chemical class N1N=CC=C2N=CC=C21 YTJAMOLQXDNLJC-UHFFFAOYSA-N 0.000 title claims abstract description 39
• 125000003710 aryl alkyl group Chemical group 0.000 title description 4
• 125000004475 heteroaralkyl group Chemical group 0.000 title 1
• 150000003839 salts Chemical class 0.000 claims abstract description 65
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 30
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 20
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 20
• 125000004434 sulfur atom Chemical group 0.000 claims abstract description 18
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 8
• 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 8
• 239000003814 drug Substances 0.000 claims abstract description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 3
• -1 3-phenyl-2-propenyl group Chemical group 0.000 claims description 217
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 39
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
• 239000000460 chlorine Chemical group 0.000 claims description 32
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 26
• 229910052801 chlorine Chemical group 0.000 claims description 24
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 20
• 239000011737 fluorine Substances 0.000 claims description 20
• 229910052731 fluorine Inorganic materials 0.000 claims description 20
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 17
• 125000004076 pyridyl group Chemical group 0.000 claims description 16
• 125000001424 substituent group Chemical group 0.000 claims description 16
• 125000001153 fluoro group Chemical group F* 0.000 claims description 15
• 125000001544 thienyl group Chemical group 0.000 claims description 15
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 14
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 14
• 125000005843 halogen group Chemical group 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• 125000006017 1-propenyl group Chemical group 0.000 claims description 11
• 125000002541 furyl group Chemical group 0.000 claims description 11
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 claims description 10
• 125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims description 10
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 10
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
• 125000003342 alkenyl group Chemical group 0.000 claims description 9
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 229910052736 halogen Inorganic materials 0.000 claims description 9
• 238000011282 treatment Methods 0.000 claims description 8
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 7
• 206010052428 Wound Diseases 0.000 claims description 6
• 208000027418 Wounds and injury Diseases 0.000 claims description 6
• 230000002265 prevention Effects 0.000 claims description 6
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 6
• 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 5
• 239000004480 active ingredient Substances 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
• 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 3
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
• QADWCDAEVLESHG-UHFFFAOYSA-N 1-(cyclopropylmethyl)-7-[(4-fluorophenyl)methoxy]-2,3-dimethylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC3CC3)C(C)=C(C)C2=CN=NC=1OCC1=CC=C(F)C=C1 QADWCDAEVLESHG-UHFFFAOYSA-N 0.000 claims description 3
• ZQVCXPORJIPTJT-UHFFFAOYSA-N 1-(cyclopropylmethyl)-7-[2-(4-fluorophenyl)ethyl]-2,3-dimethylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC3CC3)C(C)=C(C)C2=CN=NC=1CCC1=CC=C(F)C=C1 ZQVCXPORJIPTJT-UHFFFAOYSA-N 0.000 claims description 3
• WHPRSSXXCMZXNM-UHFFFAOYSA-N 1-but-2-enyl-3-ethyl-7-[(4-fluorophenyl)methoxy]-2-methylpyrrolo[2,3-d]pyridazine Chemical compound N1=NC=C2C(CC)=C(C)N(CC=CC)C2=C1OCC1=CC=C(F)C=C1 WHPRSSXXCMZXNM-UHFFFAOYSA-N 0.000 claims description 3
• RIMLLRVAYHCKRC-UHFFFAOYSA-N 1-but-2-enyl-7-[(2,4-difluorophenyl)methylsulfanyl]-2,3-dimethylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC=CC)C(C)=C(C)C2=CN=NC=1SCC1=CC=C(F)C=C1F RIMLLRVAYHCKRC-UHFFFAOYSA-N 0.000 claims description 3
• CEKZETUBQDKQKA-UHFFFAOYSA-N 1-but-2-enyl-7-[(2-chloro-6-fluorophenyl)methoxy]-2,3-dimethylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC=CC)C(C)=C(C)C2=CN=NC=1OCC1=C(F)C=CC=C1Cl CEKZETUBQDKQKA-UHFFFAOYSA-N 0.000 claims description 3
• OTTJCBSOOXSILK-UHFFFAOYSA-N 1-but-2-enyl-7-[(4-chloro-2-fluorophenyl)methoxy]-2,3-dimethylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC=CC)C(C)=C(C)C2=CN=NC=1OCC1=CC=C(Cl)C=C1F OTTJCBSOOXSILK-UHFFFAOYSA-N 0.000 claims description 3
• GQWAISYMVMPUJT-UHFFFAOYSA-N 1-but-2-enyl-7-[(4-fluorophenyl)methylsulfanyl]-2,3-dimethylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC=CC)C(C)=C(C)C2=CN=NC=1SCC1=CC=C(F)C=C1 GQWAISYMVMPUJT-UHFFFAOYSA-N 0.000 claims description 3
• VZNVPNIPSXHAKB-UHFFFAOYSA-N 1-but-2-enyl-7-[2-(2,4-difluorophenyl)ethyl]-2,3-dimethylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC=CC)C(C)=C(C)C2=CN=NC=1CCC1=CC=C(F)C=C1F VZNVPNIPSXHAKB-UHFFFAOYSA-N 0.000 claims description 3
• BANSVOHTSGFJJX-UHFFFAOYSA-N 1-but-2-enyl-7-[2-(4-fluorophenyl)ethyl]-2,3-dimethylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC=CC)C(C)=C(C)C2=CN=NC=1CCC1=CC=C(F)C=C1 BANSVOHTSGFJJX-UHFFFAOYSA-N 0.000 claims description 3
• HXFOUQHOORUXBU-UHFFFAOYSA-N 2,3-dimethyl-7-(2-phenylethyl)-1-prop-2-enylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC=C)C(C)=C(C)C2=CN=NC=1CCC1=CC=CC=C1 HXFOUQHOORUXBU-UHFFFAOYSA-N 0.000 claims description 3
• HLJNAZVBCOSFAA-UHFFFAOYSA-N 2,3-dimethyl-7-phenylmethoxy-1-prop-2-ynylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC#C)C(C)=C(C)C2=CN=NC=1OCC1=CC=CC=C1 HLJNAZVBCOSFAA-UHFFFAOYSA-N 0.000 claims description 3
• QDIQGIQRIPEDTK-UHFFFAOYSA-N 7-[(2,4-difluorophenyl)methoxy]-2,3-dimethyl-1-prop-2-enylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC=C)C(C)=C(C)C2=CN=NC=1OCC1=CC=C(F)C=C1F QDIQGIQRIPEDTK-UHFFFAOYSA-N 0.000 claims description 3
• NXPLYKRKIFPEOA-UHFFFAOYSA-N 7-[(4-fluorophenyl)methoxy]-2,3-dimethyl-1-[(2-methylcyclopropyl)methyl]pyrrolo[2,3-d]pyridazine Chemical compound CC1CC1CN1C2=C(OCC=3C=CC(F)=CC=3)N=NC=C2C(C)=C1C NXPLYKRKIFPEOA-UHFFFAOYSA-N 0.000 claims description 3
• XOKYGQZKRMWWLC-UHFFFAOYSA-N 7-[(4-fluorophenyl)methylsulfanyl]-2,3-dimethyl-1-prop-2-enylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC=C)C(C)=C(C)C2=CN=NC=1SCC1=CC=C(F)C=C1 XOKYGQZKRMWWLC-UHFFFAOYSA-N 0.000 claims description 3
• ZSNQOZPVTLLTAP-UHFFFAOYSA-N 7-[2-(2,4-difluorophenyl)ethyl]-2,3-dimethyl-1-prop-2-enylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC=C)C(C)=C(C)C2=CN=NC=1CCC1=CC=C(F)C=C1F ZSNQOZPVTLLTAP-UHFFFAOYSA-N 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 125000006726 (C1-C5) alkenyl group Chemical group 0.000 claims description 2
• UFDJGLZCSDYEPZ-UHFFFAOYSA-N 1-(cyclopropylmethyl)-7-[2-(2,4-difluorophenyl)ethyl]-2,3-dimethylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC3CC3)C(C)=C(C)C2=CN=NC=1CCC1=CC=C(F)C=C1F UFDJGLZCSDYEPZ-UHFFFAOYSA-N 0.000 claims description 2
• APYJMPFHBAIIJU-UHFFFAOYSA-N 1-but-2-enyl-2,3-dimethyl-7-phenylmethoxypyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC=CC)C(C)=C(C)C2=CN=NC=1OCC1=CC=CC=C1 APYJMPFHBAIIJU-UHFFFAOYSA-N 0.000 claims description 2
• UXVGZBIXIIZXOQ-UHFFFAOYSA-N 1-but-2-enyl-7-[(2,4-dichlorophenyl)methoxy]-2,3-dimethylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC=CC)C(C)=C(C)C2=CN=NC=1OCC1=CC=C(Cl)C=C1Cl UXVGZBIXIIZXOQ-UHFFFAOYSA-N 0.000 claims description 2
• OOHBUEABHBOJJQ-UHFFFAOYSA-N 1-but-2-enyl-7-[(4-fluorophenyl)methoxy]-2,3-dimethyl-5-oxidopyrrolo[2,3-d]pyridazin-5-ium Chemical compound C=12N(CC=CC)C(C)=C(C)C2=C[N+]([O-])=NC=1OCC1=CC=C(F)C=C1 OOHBUEABHBOJJQ-UHFFFAOYSA-N 0.000 claims description 2
• KIUORNGKRGLROA-UHFFFAOYSA-N 1-but-2-enyl-7-[(4-fluorophenyl)methoxy]-2,3-dimethylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC=CC)C(C)=C(C)C2=CN=NC=1OCC1=CC=C(F)C=C1 KIUORNGKRGLROA-UHFFFAOYSA-N 0.000 claims description 2
• HNORUNBXDVOQJC-UHFFFAOYSA-N 7-[(2,4-difluorophenyl)methoxy]-2,3-dimethyl-1-[(2-methylcyclopropyl)methyl]pyrrolo[2,3-d]pyridazine Chemical compound CC1CC1CN1C2=C(OCC=3C(=CC(F)=CC=3)F)N=NC=C2C(C)=C1C HNORUNBXDVOQJC-UHFFFAOYSA-N 0.000 claims description 2
• VMFGTNOLRKEWNB-UHFFFAOYSA-N 7-[(2-fluorophenyl)methoxy]-2,3-dimethyl-1-prop-2-enylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC=C)C(C)=C(C)C2=CN=NC=1OCC1=CC=CC=C1F VMFGTNOLRKEWNB-UHFFFAOYSA-N 0.000 claims description 2
• XYWWGPRLAXSSKZ-UHFFFAOYSA-N 7-[(4-fluorophenyl)methoxy]-2,3-dimethyl-1-prop-1-enylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(C=CC)C(C)=C(C)C2=CN=NC=1OCC1=CC=C(F)C=C1 XYWWGPRLAXSSKZ-UHFFFAOYSA-N 0.000 claims description 2
• MZBYYTSYUWDHPO-UHFFFAOYSA-N 7-[(4-fluorophenyl)methoxy]-2,3-dimethyl-1-prop-2-enylpyrrolo[2,3-d]pyridazine Chemical compound C=12N(CC=C)C(C)=C(C)C2=CN=NC=1OCC1=CC=C(F)C=C1 MZBYYTSYUWDHPO-UHFFFAOYSA-N 0.000 claims description 2
• 208000025865 Ulcer Diseases 0.000 claims description 2
• 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 2
• PBDUABWJXXJBNQ-UHFFFAOYSA-N 1-but-2-enyl-7-[2-(2,4-difluorophenyl)ethyl]-2,3-dimethyl-6-oxidopyrrolo[2,3-d]pyridazin-6-ium Chemical compound C=12N(CC=CC)C(C)=C(C)C2=CN=[N+]([O-])C=1CCC1=CC=C(F)C=C1F PBDUABWJXXJBNQ-UHFFFAOYSA-N 0.000 claims 1
• OFTROUGHZPGPDW-UHFFFAOYSA-N 2,3-dimethyl-1-[(2-methylcyclopropyl)methyl]-7-(2-phenylethyl)pyrrolo[2,3-d]pyridazine Chemical compound CC1CC1CN1C2=C(CCC=3C=CC=CC=3)N=NC=C2C(C)=C1C OFTROUGHZPGPDW-UHFFFAOYSA-N 0.000 claims 1
• ZRJMWGWSSWVIIL-UHFFFAOYSA-N 7-[2-(4-fluorophenyl)ethyl]-2,3-dimethyl-1-[(2-methylcyclopropyl)methyl]pyrrolo[2,3-d]pyridazine Chemical compound CC1CC1CN1C2=C(CCC=3C=CC(F)=CC=3)N=NC=C2C(C)=C1C ZRJMWGWSSWVIIL-UHFFFAOYSA-N 0.000 claims 1
• 241001136616 Methone Species 0.000 claims 1
• 125000003545 alkoxy group Chemical group 0.000 claims 1
• 239000005557 antagonist Substances 0.000 claims 1
• 239000000729 antidote Substances 0.000 claims 1
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
• 231100000397 ulcer Toxicity 0.000 claims 1
• 230000002496 gastric effect Effects 0.000 abstract description 20
• 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 12
• 230000028327 secretion Effects 0.000 abstract description 12
• 229910052760 oxygen Inorganic materials 0.000 abstract description 9
• 239000001301 oxygen Substances 0.000 abstract description 9
• 241000590002 Helicobacter pylori Species 0.000 abstract description 8
• 230000000844 anti-bacterial effect Effects 0.000 abstract description 8
• 229940037467 helicobacter pylori Drugs 0.000 abstract description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 7
• 125000000041 C6-C10 aryl group Chemical group 0.000 abstract description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 6
• 230000002401 inhibitory effect Effects 0.000 abstract description 6
• 201000010099 disease Diseases 0.000 abstract description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 5
• 210000001156 gastric mucosa Anatomy 0.000 abstract description 4
• 125000005842 heteroatom Chemical group 0.000 abstract description 4
• 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
• 230000001681 protective effect Effects 0.000 abstract description 3
• 125000002947 alkylene group Chemical group 0.000 abstract description 2
• 230000003449 preventive effect Effects 0.000 abstract description 2
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 abstract 1
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
• 239000011593 sulfur Substances 0.000 abstract 1
• 229940124597 therapeutic agent Drugs 0.000 abstract 1
• 150000001875 compounds Chemical class 0.000 description 367
• 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 265
• 238000000034 method Methods 0.000 description 223
• 238000001819 mass spectrum Methods 0.000 description 198
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 142
• UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 130
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 116
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
• 239000000843 powder Substances 0.000 description 83
• 239000000203 mixture Substances 0.000 description 78
• 238000000921 elemental analysis Methods 0.000 description 77
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
• 239000013078 crystal Substances 0.000 description 64
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 62
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 57
• 239000000243 solution Substances 0.000 description 56
• 239000002904 solvent Substances 0.000 description 49
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
• 239000003921 oil Substances 0.000 description 39
• 235000019198 oils Nutrition 0.000 description 39
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 38
• 101150065749 Churc1 gene Proteins 0.000 description 38
• 102100038239 Protein Churchill Human genes 0.000 description 38
• 238000006243 chemical reaction Methods 0.000 description 38
• 238000005481 NMR spectroscopy Methods 0.000 description 34
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
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• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
• 238000004440 column chromatography Methods 0.000 description 22
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 22
• 230000002829 reductive effect Effects 0.000 description 22
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
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• CGIUBTMVMYIEJB-UHFFFAOYSA-N 1-but-2-enyl-7-chloro-2,3-dimethylpyrrolo[2,3-d]pyridazine Chemical compound N1=NC(Cl)=C2N(CC=CC)C(C)=C(C)C2=C1 CGIUBTMVMYIEJB-UHFFFAOYSA-N 0.000 description 20
• JRSRSELFXJTQBX-UHFFFAOYSA-N methyl 3-formyl-4,5-dimethyl-1h-pyrrole-2-carboxylate Chemical compound COC(=O)C=1NC(C)=C(C)C=1C=O JRSRSELFXJTQBX-UHFFFAOYSA-N 0.000 description 20
• 235000019445 benzyl alcohol Nutrition 0.000 description 19
• 239000000284 extract Substances 0.000 description 19
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• 239000000741 silica gel Substances 0.000 description 18
• 229910002027 silica gel Inorganic materials 0.000 description 18
• 239000007787 solid Substances 0.000 description 18
• 239000005457 ice water Substances 0.000 description 16
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• 238000002360 preparation method Methods 0.000 description 15
• 150000002170 ethers Chemical class 0.000 description 14
• 238000001914 filtration Methods 0.000 description 14
• 239000012442 inert solvent Substances 0.000 description 14
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
• LJXPWUAAAAXJBX-UHFFFAOYSA-N 2-methylallyl radical Chemical compound [CH2]C(C)=C LJXPWUAAAAXJBX-UHFFFAOYSA-N 0.000 description 13
• GEZMEIHVFSWOCA-UHFFFAOYSA-N (4-fluorophenyl)methanol Chemical compound OCC1=CC=C(F)C=C1 GEZMEIHVFSWOCA-UHFFFAOYSA-N 0.000 description 12
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
• 239000010502 orange oil Substances 0.000 description 12
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• KEWBZECQHBPHFJ-UHFFFAOYSA-N methyl 1-(2-bromoethyl)-3-formyl-4,5-dimethylpyrrole-2-carboxylate Chemical compound COC(=O)C1=C(C=O)C(C)=C(C)N1CCBr KEWBZECQHBPHFJ-UHFFFAOYSA-N 0.000 description 2
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• RJMRSNAUWIRWDG-UHFFFAOYSA-N methyl 1-(3-fluoropropyl)-3-formyl-4,5-dimethylpyrrole-2-carboxylate Chemical compound COC(=O)C1=C(C=O)C(C)=C(C)N1CCCF RJMRSNAUWIRWDG-UHFFFAOYSA-N 0.000 description 2
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• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
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• 229910000105 potassium hydride Inorganic materials 0.000 description 2
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• 230000003389 potentiating effect Effects 0.000 description 2
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