SK284914B6 - Deriváty 4a,5a,8a,8b-tetrahydro-6H-pyrolo[3',4':4,5]furo-[3,2-b] pyridín-6,8(7H)-diónu na hubenie endoparazitov a spôsob ich výroby - Google Patents

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Publication number

SK284914B6

SK284914B6 SK492-98A SK49298A SK284914B6 SK 284914 B6 SK284914 B6 SK 284914B6 SK 49298 A SK49298 A SK 49298A SK 284914 B6 SK284914 B6 SK 284914B6

Authority

SK

Slovakia

Prior art keywords

carbon atoms

group

alkyl

cycloalkyl

formula

Prior art date

1995-10-19

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• 238000000034 method Methods 0.000 title claims abstract description 151
• YOXJWRUWHFBVJZ-UHFFFAOYSA-N 4a,5a,8a,8b-tetrahydropyrrolo[2,3]furo[2,4-b]pyridine-6,8-dione Chemical class C1=CC=NC2C3C(=O)NC(=O)C3OC21 YOXJWRUWHFBVJZ-UHFFFAOYSA-N 0.000 title claims abstract description 18
• 244000079386 endoparasite Species 0.000 title claims abstract description 13
• 238000002360 preparation method Methods 0.000 claims abstract description 27
• 125000004432 carbon atom Chemical group C* 0.000 claims description 587
• -1 sulfoxy Chemical group 0.000 claims description 453
• 125000000217 alkyl group Chemical group 0.000 claims description 303
• 150000001875 compounds Chemical class 0.000 claims description 188
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 125
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 113
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 103
• 238000006243 chemical reaction Methods 0.000 claims description 77
• 125000001072 heteroaryl group Chemical group 0.000 claims description 69
• 239000003085 diluting agent Substances 0.000 claims description 68
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 61
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 57
• 229910052757 nitrogen Inorganic materials 0.000 claims description 53
• 125000003118 aryl group Chemical group 0.000 claims description 51
• 125000003545 alkoxy group Chemical group 0.000 claims description 50
• 150000003839 salts Chemical class 0.000 claims description 50
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 42
• 125000003342 alkenyl group Chemical group 0.000 claims description 41
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 39
• 239000003153 chemical reaction reagent Substances 0.000 claims description 39
• 238000004519 manufacturing process Methods 0.000 claims description 39
• 229910052739 hydrogen Inorganic materials 0.000 claims description 38
• 239000000203 mixture Substances 0.000 claims description 38
• 229910052717 sulfur Inorganic materials 0.000 claims description 37
• 125000001188 haloalkyl group Chemical group 0.000 claims description 35
• 239000001257 hydrogen Substances 0.000 claims description 35
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 34
• 239000003054 catalyst Substances 0.000 claims description 33
• 125000004122 cyclic group Chemical group 0.000 claims description 33
• 125000000304 alkynyl group Chemical group 0.000 claims description 32
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 31
• 239000002253 acid Substances 0.000 claims description 29
• 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 28
• 239000000460 chlorine Substances 0.000 claims description 28
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 27
• 125000004434 sulfur atom Chemical group 0.000 claims description 27
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 26
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 25
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 25
• 125000004423 acyloxy group Chemical group 0.000 claims description 25
• 125000003282 alkyl amino group Chemical group 0.000 claims description 25
• 229910052801 chlorine Inorganic materials 0.000 claims description 25
• 239000011737 fluorine Substances 0.000 claims description 25
• 229910052731 fluorine Inorganic materials 0.000 claims description 25
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 25
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 24
• 125000004414 alkyl thio group Chemical group 0.000 claims description 24
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 23
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 23
• 229910052794 bromium Inorganic materials 0.000 claims description 23
• 125000003277 amino group Chemical group 0.000 claims description 21
• 125000004429 atom Chemical group 0.000 claims description 21
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 21
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 20
• 125000005843 halogen group Chemical group 0.000 claims description 20
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 19
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 18
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 17
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 16
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 15
• 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 15
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 15
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 14
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 14
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
• SPUVAXLBKAXYLU-UHFFFAOYSA-N 1,2,4a,5a,8a,8b-hexahydropyrrolo[2,3]furo[2,4-b]pyridine-6,8-dione Chemical compound N1CC=CC2OC3C(=O)NC(=O)C3C21 SPUVAXLBKAXYLU-UHFFFAOYSA-N 0.000 claims description 12
• 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 12
• 239000011230 binding agent Substances 0.000 claims description 12
• 239000003795 chemical substances by application Substances 0.000 claims description 12
• 230000003287 optical effect Effects 0.000 claims description 12
• YNQGQYOTKRILCL-UHFFFAOYSA-N 1,2,3,4,4a,5a,8a,8b-octahydropyrrolo[2,3]furo[2,4-b]pyridine-6,8-dione Chemical compound N1CCCC2OC3C(=O)NC(=O)C3C21 YNQGQYOTKRILCL-UHFFFAOYSA-N 0.000 claims description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 11
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
• 239000013543 active substance Substances 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 11
• 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 11
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
• 239000002168 alkylating agent Substances 0.000 claims description 10
• 229940100198 alkylating agent Drugs 0.000 claims description 10
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 10
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 9
• 125000002837 carbocyclic group Chemical group 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 239000001569 carbon dioxide Substances 0.000 claims description 9
• 229910002092 carbon dioxide Inorganic materials 0.000 claims description 9
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
• 125000002950 monocyclic group Chemical group 0.000 claims description 9
• 125000003107 substituted aryl group Chemical group 0.000 claims description 9
• 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 8
• 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 239000011591 potassium Substances 0.000 claims description 8
• 229910052700 potassium Inorganic materials 0.000 claims description 8
• 125000001424 substituent group Chemical group 0.000 claims description 8
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 7
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
• 150000007513 acids Chemical class 0.000 claims description 7
• 229910052783 alkali metal Inorganic materials 0.000 claims description 7
• 125000004104 aryloxy group Chemical group 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 7
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• 125000004962 sulfoxyl group Chemical group 0.000 claims description 7
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 125000002619 bicyclic group Chemical group 0.000 claims description 6
• 150000002118 epoxides Chemical class 0.000 claims description 6
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
• 229910052708 sodium Inorganic materials 0.000 claims description 6
• 239000011734 sodium Substances 0.000 claims description 6
• 239000011593 sulfur Chemical group 0.000 claims description 6
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
• 125000002252 acyl group Chemical group 0.000 claims description 5
• 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 5
• 150000008041 alkali metal carbonates Chemical class 0.000 claims description 5
• 150000003862 amino acid derivatives Chemical class 0.000 claims description 5
• 229910052792 caesium Inorganic materials 0.000 claims description 5
• TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 5
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 5
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 5
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 4
• 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 4
• 229910052744 lithium Inorganic materials 0.000 claims description 4
• 125000004971 nitroalkyl group Chemical group 0.000 claims description 4
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 4
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 4
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• 150000001204 N-oxides Chemical class 0.000 claims description 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 3
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
• 239000004094 surface-active agent Substances 0.000 claims description 3
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
• 239000000945 filler Substances 0.000 claims description 2
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims description 2
• 239000011976 maleic acid Substances 0.000 claims description 2
• 229910021645 metal ion Inorganic materials 0.000 claims description 2
• 238000011084 recovery Methods 0.000 claims description 2
• IDBGELBXQVAXNR-UHFFFAOYSA-N N=1C2C(C=CC1)OC1C2C=NC1 Chemical class N=1C2C(C=CC1)OC1C2C=NC1 IDBGELBXQVAXNR-UHFFFAOYSA-N 0.000 claims 1
• 150000001340 alkali metals Chemical class 0.000 claims 1
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 1
• 125000002560 nitrile group Chemical group 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 49
• 239000000243 solution Substances 0.000 description 47
• 150000003254 radicals Chemical class 0.000 description 46
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 45
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 36
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
• 239000011541 reaction mixture Substances 0.000 description 31
• 239000007858 starting material Substances 0.000 description 30
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 28
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 25
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 24
• 239000012074 organic phase Substances 0.000 description 22
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
• 238000005984 hydrogenation reaction Methods 0.000 description 21
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 20
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 19
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 19
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
• 239000002585 base Substances 0.000 description 18
• 238000002451 electron ionisation mass spectrometry Methods 0.000 description 18
• 235000019441 ethanol Nutrition 0.000 description 18
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 18
• 239000002904 solvent Substances 0.000 description 18
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 17
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 17
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 17
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 17
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 16
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 16
• 238000005160 1H NMR spectroscopy Methods 0.000 description 15
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
• 239000012043 crude product Substances 0.000 description 15
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 15
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
• 230000035484 reaction time Effects 0.000 description 15
• 229920001577 copolymer Polymers 0.000 description 13
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 13
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 12
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 12
• 239000002245 particle Substances 0.000 description 12
• 239000000047 product Substances 0.000 description 12
• 239000000741 silica gel Substances 0.000 description 12
• 229910002027 silica gel Inorganic materials 0.000 description 12
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 12
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 11
• 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 description 11
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 11
• 229920002554 vinyl polymer Polymers 0.000 description 11
• 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 10
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
• 241001465754 Metazoa Species 0.000 description 10
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
• 239000004480 active ingredient Substances 0.000 description 10
• 230000002829 reductive effect Effects 0.000 description 10
• 239000000126 substance Substances 0.000 description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
• 230000002378 acidificating effect Effects 0.000 description 9
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 9
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 9
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 9
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 9
• 229910052938 sodium sulfate Inorganic materials 0.000 description 9
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