NO890723L - Fremgangsmaate for fremstilling av terapeutisk aktive 3-alkenyl-1-azabicyklo 3.2.0 hept-2-en-2-karboksylsyrederivater - Google Patents

Info

Publication number

NO890723L

NO890723L NO89890723A NO890723A NO890723L NO 890723 L NO890723 L NO 890723L NO 89890723 A NO89890723 A NO 89890723A NO 890723 A NO890723 A NO 890723A NO 890723 L NO890723 L NO 890723L

Authority

NO

Norway

Prior art keywords

alkyl

oxo

hydroxy

pyrrolidinyl

compound

Prior art date

1988-02-22

Links

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• 238000002360 preparation method Methods 0.000 title claims abstract description 59
• 238000000034 method Methods 0.000 title claims abstract description 50
• 230000001225 therapeutic effect Effects 0.000 title claims description 3
• FYZUENZXIZCLAZ-UHFFFAOYSA-N 2-methylhept-2-enoic acid Chemical class CCCCC=C(C)C(O)=O FYZUENZXIZCLAZ-UHFFFAOYSA-N 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 130
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 96
• 150000003839 salts Chemical class 0.000 claims abstract description 92
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 78
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 40
• 125000001931 aliphatic group Chemical group 0.000 claims abstract description 36
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 32
• 125000001424 substituent group Chemical group 0.000 claims abstract description 32
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
• 239000001257 hydrogen Substances 0.000 claims abstract description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
• -1 imino, protected imino Chemical group 0.000 claims description 159
• 238000006243 chemical reaction Methods 0.000 claims description 108
• 238000004519 manufacturing process Methods 0.000 claims description 96
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 91
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 71
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 42
• 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 35
• 125000003282 alkyl amino group Chemical group 0.000 claims description 34
• 125000006239 protecting group Chemical group 0.000 claims description 26
• 125000003545 alkoxy group Chemical group 0.000 claims description 24
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 21
• 229920006395 saturated elastomer Polymers 0.000 claims description 17
• 125000001589 carboacyl group Chemical group 0.000 claims description 15
• 238000003379 elimination reaction Methods 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 125000001118 alkylidene group Chemical group 0.000 claims description 8
• 125000002393 azetidinyl group Chemical group 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 229910052736 halogen Inorganic materials 0.000 claims description 8
• 150000002367 halogens Chemical class 0.000 claims description 8
• 125000002757 morpholinyl group Chemical group 0.000 claims description 8
• 125000003386 piperidinyl group Chemical group 0.000 claims description 8
• 239000007858 starting material Substances 0.000 claims description 8
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 6
• 125000006501 nitrophenyl group Chemical group 0.000 claims description 6
• 125000003118 aryl group Chemical group 0.000 claims description 5
• 208000035473 Communicable disease Diseases 0.000 claims description 4
• 125000002252 acyl group Chemical group 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• 239000007983 Tris buffer Substances 0.000 claims description 3
• 125000004423 acyloxy group Chemical group 0.000 claims description 3
• LKPRWOHCDHOEKA-KFVIUVKUSA-N (5r,6s)-3-[(e)-1-[(2s)-1-ethanimidoylpyrrolidin-2-yl]prop-1-en-2-yl]-6-[(1r)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1\C(C)=C\[C@@H]1CCCN1C(C)=N LKPRWOHCDHOEKA-KFVIUVKUSA-N 0.000 claims description 2
• VGRNUFZNEAPZOX-AKBFKNQKSA-N (5r,6s)-3-[1-[(2s)-4-fluoropyrrolidin-2-yl]prop-1-en-2-yl]-6-[(1r)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1C(C)=C[C@@H]1CC(F)CN1 VGRNUFZNEAPZOX-AKBFKNQKSA-N 0.000 claims description 2
• AIHFDCWNIOUGRR-IPVWOEAWSA-N (5r,6s)-6-[(1r)-1-hydroxyethyl]-3-[(e)-1-[(2s)-1-methanimidoylpyrrolidin-2-yl]prop-1-en-2-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1\C(C)=C\[C@@H]1CCCN1C=N AIHFDCWNIOUGRR-IPVWOEAWSA-N 0.000 claims description 2
• FPNXBYFOEHIACE-ZMJPVWNMSA-N (5r,6s)-6-[(1r)-1-hydroxyethyl]-3-[1-[(2s)-4-methylidenepyrrolidin-2-yl]prop-1-en-2-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1C(C)=C[C@@H]1CC(=C)CN1 FPNXBYFOEHIACE-ZMJPVWNMSA-N 0.000 claims description 2
• JLPYTLCZYYWTPX-IQOUGMIPSA-N (5r,6s)-6-[(1r)-1-hydroxyethyl]-3-[1-[(2s)-5-imino-1-methylpyrrolidin-2-yl]prop-1-en-2-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1C(C)=C[C@@H]1CCC(=N)N1C JLPYTLCZYYWTPX-IQOUGMIPSA-N 0.000 claims description 2
• UALMGHTWALJBPS-AIPRNEOBSA-N (5r,6s)-6-[(1r)-1-hydroxyethyl]-3-[1-[(2s,4r)-4-hydroxypyrrolidin-2-yl]prop-1-en-2-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1C(C)=C[C@@H]1C[C@@H](O)CN1 UALMGHTWALJBPS-AIPRNEOBSA-N 0.000 claims description 2
• ILYOSWMNJBHNDK-JIFFNSBPSA-N (5r,6s)-6-[(1r)-1-hydroxyethyl]-3-[1-[(2s,4r)-4-methoxypyrrolidin-2-yl]prop-1-en-2-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C1[C@@H](OC)CN[C@@H]1C=C(C)C1=C(C(O)=O)N2C(=O)[C@H]([C@@H](C)O)[C@H]2C1 ILYOSWMNJBHNDK-JIFFNSBPSA-N 0.000 claims description 2
• UALMGHTWALJBPS-UWHIDBLNSA-N (5r,6s)-6-[(1r)-1-hydroxyethyl]-3-[1-[(2s,4s)-4-hydroxypyrrolidin-2-yl]prop-1-en-2-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1C(C)=C[C@@H]1C[C@H](O)CN1 UALMGHTWALJBPS-UWHIDBLNSA-N 0.000 claims description 2
• DCCTYRCNLWRSTN-UMXNBRPZSA-N (5r,6s)-6-[(1r)-1-hydroxyethyl]-3-[1-[5-(methoxymethyl)pyrrolidin-2-yl]prop-1-en-2-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound N1C(COC)CCC1C=C(C)C1=C(C(O)=O)N2C(=O)[C@H]([C@@H](C)O)[C@H]2C1 DCCTYRCNLWRSTN-UMXNBRPZSA-N 0.000 claims description 2
• HARJKPDPGACOGE-NJGBWHNRSA-N (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-(1-pyrrolidin-3-ylprop-1-en-2-yl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1C(C)=CC1CCNC1 HARJKPDPGACOGE-NJGBWHNRSA-N 0.000 claims description 2
• WIHJTRXAYSNDID-QBWCJWQGSA-N (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(e)-2-[(2s)-pyrrolidin-2-yl]ethenyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1\C=C\[C@@H]1CCCN1 WIHJTRXAYSNDID-QBWCJWQGSA-N 0.000 claims description 2
• 241001465754 Metazoa Species 0.000 claims description 2
• DZXZGWCXNJTJSR-JIFFNSBPSA-N O[C@H](C)[C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)C(=C[C@H]1NC[C@@H](C1)OC(NC)=O)C Chemical compound O[C@H](C)[C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)C(=C[C@H]1NC[C@@H](C1)OC(NC)=O)C DZXZGWCXNJTJSR-JIFFNSBPSA-N 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• QKCQDKXUTBLEKD-BAXYUMHFSA-N (5r,6s)-6-[(1r)-1-hydroxyethyl]-3-[1-[5-(hydroxymethyl)pyrrolidin-2-yl]propan-2-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1C(C)CC1CCC(CO)N1 QKCQDKXUTBLEKD-BAXYUMHFSA-N 0.000 claims 1
• 239000003814 drug Substances 0.000 claims 1
• 229940079593 drug Drugs 0.000 claims 1
• DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](C(=O)N(C)C)C1 DMJNNHOOLUXYBV-PQTSNVLCSA-N 0.000 claims 1
• 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims 1
• 239000004480 active ingredient Substances 0.000 abstract description 2
• 239000003937 drug carrier Substances 0.000 abstract description 2
• 239000000546 pharmaceutical excipient Substances 0.000 abstract description 2
• 239000008194 pharmaceutical composition Substances 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 390
• 239000000203 mixture Substances 0.000 description 205
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 141
• 239000000243 solution Substances 0.000 description 131
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 118
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 112
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 109
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 90
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
• 238000003756 stirring Methods 0.000 description 64
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 59
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 58
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 57
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 56
• 235000019341 magnesium sulphate Nutrition 0.000 description 56
• 239000012267 brine Substances 0.000 description 55
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 55
• 239000002904 solvent Substances 0.000 description 53
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 52
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 50
• 239000000741 silica gel Substances 0.000 description 50
• 229910002027 silica gel Inorganic materials 0.000 description 50
• 239000012074 organic phase Substances 0.000 description 46
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 42
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 42
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
• 239000011541 reaction mixture Substances 0.000 description 32
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
• 150000002148 esters Chemical group 0.000 description 24
• 239000000460 chlorine Substances 0.000 description 22
• 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 22
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
• 238000001704 evaporation Methods 0.000 description 21
• 230000008020 evaporation Effects 0.000 description 21
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 20
• 235000017557 sodium bicarbonate Nutrition 0.000 description 20
• HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 18
• 238000001816 cooling Methods 0.000 description 18
• 229910052760 oxygen Inorganic materials 0.000 description 18
• 229910052717 sulfur Inorganic materials 0.000 description 18
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
• 238000010438 heat treatment Methods 0.000 description 17
• WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 16
• 239000000706 filtrate Substances 0.000 description 16
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 16
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
• 230000009931 harmful effect Effects 0.000 description 15
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
• 239000002244 precipitate Substances 0.000 description 14
• 239000002585 base Substances 0.000 description 13
• 229910000027 potassium carbonate Inorganic materials 0.000 description 13
• 235000011181 potassium carbonates Nutrition 0.000 description 13
• 239000002253 acid Substances 0.000 description 12
• 239000008346 aqueous phase Substances 0.000 description 12
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
• 235000011054 acetic acid Nutrition 0.000 description 11
• 238000001914 filtration Methods 0.000 description 11
• 239000006188 syrup Substances 0.000 description 11
• 235000020357 syrup Nutrition 0.000 description 11
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 10
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
• 230000007062 hydrolysis Effects 0.000 description 10
• 238000006460 hydrolysis reaction Methods 0.000 description 10
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
• CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 10
• 238000006722 reduction reaction Methods 0.000 description 10
• 239000008096 xylene Substances 0.000 description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 9
• 229910052783 alkali metal Inorganic materials 0.000 description 9
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
• SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 8
• JDYOMWDXAAPCEE-UHFFFAOYSA-N 3-(triphenyl-$l^{5}-phosphanylidene)butan-2-one Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C(C)C(=O)C)C1=CC=CC=C1 JDYOMWDXAAPCEE-UHFFFAOYSA-N 0.000 description 8
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
• 125000005907 alkyl ester group Chemical group 0.000 description 8
• HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 8
• 238000010992 reflux Methods 0.000 description 8
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• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
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• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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