DE2406930A1 - Neue heterocyclische verbindungen und verfahren zu ihrer herstellung - Google Patents

Info

Publication number

DE2406930A1

DE2406930A1 DE19742406930 DE2406930A DE2406930A1 DE 2406930 A1 DE2406930 A1 DE 2406930A1 DE 19742406930 DE19742406930 DE 19742406930 DE 2406930 A DE2406930 A DE 2406930A DE 2406930 A1 DE2406930 A1 DE 2406930A1

Authority

DE

Germany

Prior art keywords

lower alkyl

carbon atoms

formula

alkoxy

compounds

Prior art date

1973-02-20

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.)

Ceased

Links

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• 238000000034 method Methods 0.000 title claims description 100
• 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 4
• 238000004519 manufacturing process Methods 0.000 title description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 653
• 125000004432 carbon atom Chemical group C* 0.000 claims description 606
• -1 alkali metal cyanoborohydride Chemical class 0.000 claims description 533
• 150000001875 compounds Chemical class 0.000 claims description 190
• 125000003545 alkoxy group Chemical group 0.000 claims description 133
• 229910052739 hydrogen Inorganic materials 0.000 claims description 106
• 239000001257 hydrogen Substances 0.000 claims description 106
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 103
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 99
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 91
• 125000003342 alkenyl group Chemical group 0.000 claims description 82
• 125000003282 alkyl amino group Chemical group 0.000 claims description 77
• 150000003254 radicals Chemical class 0.000 claims description 72
• 239000007859 condensation product Substances 0.000 claims description 67
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 67
• 150000001299 aldehydes Chemical class 0.000 claims description 66
• 239000000203 mixture Substances 0.000 claims description 61
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
• 150000002431 hydrogen Chemical class 0.000 claims description 58
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 56
• 150000002576 ketones Chemical class 0.000 claims description 52
• 239000002253 acid Substances 0.000 claims description 49
• 239000003795 chemical substances by application Substances 0.000 claims description 48
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 47
• 125000004414 alkyl thio group Chemical group 0.000 claims description 46
• 229910052736 halogen Inorganic materials 0.000 claims description 44
• 150000002367 halogens Chemical class 0.000 claims description 43
• 238000006243 chemical reaction Methods 0.000 claims description 42
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 38
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 38
• 125000004442 acylamino group Chemical group 0.000 claims description 37
• 239000007858 starting material Substances 0.000 claims description 36
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 32
• 125000002947 alkylene group Chemical group 0.000 claims description 31
• 150000003839 salts Chemical class 0.000 claims description 31
• 125000001424 substituent group Chemical group 0.000 claims description 31
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 30
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 29
• 229910052757 nitrogen Inorganic materials 0.000 claims description 29
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 28
• 239000002585 base Substances 0.000 claims description 25
• 230000009467 reduction Effects 0.000 claims description 25
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 24
• 229910052801 chlorine Inorganic materials 0.000 claims description 23
• 239000000460 chlorine Substances 0.000 claims description 23
• 230000007062 hydrolysis Effects 0.000 claims description 23
• 238000006460 hydrolysis reaction Methods 0.000 claims description 23
• 150000001204 N-oxides Chemical class 0.000 claims description 22
• 229910052794 bromium Inorganic materials 0.000 claims description 22
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
• 239000003513 alkali Substances 0.000 claims description 21
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 21
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 20
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 17
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 16
• 150000004892 pyridazines Chemical class 0.000 claims description 16
• ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 16
• 150000003222 pyridines Chemical class 0.000 claims description 16
• 150000003230 pyrimidines Chemical class 0.000 claims description 16
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
• 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 15
• 239000000047 product Substances 0.000 claims description 15
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
• 238000005984 hydrogenation reaction Methods 0.000 claims description 14
• 229910052783 alkali metal Inorganic materials 0.000 claims description 13
• 150000001412 amines Chemical class 0.000 claims description 13
• 125000003277 amino group Chemical group 0.000 claims description 12
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
• 150000003216 pyrazines Chemical class 0.000 claims description 12
• 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 239000000126 substance Substances 0.000 claims description 11
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 10
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 10
• GAJBWMUZVXJIBO-UHFFFAOYSA-N 1-oxidopyridazin-1-ium Chemical class [O-][N+]1=CC=CC=N1 GAJBWMUZVXJIBO-UHFFFAOYSA-N 0.000 claims description 9
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 9
• 229910052740 iodine Inorganic materials 0.000 claims description 9
• 230000008569 process Effects 0.000 claims description 9
• RUIZBQQGWNBRFH-UHFFFAOYSA-N 1-oxidopyrazin-1-ium Chemical class [O-][N+]1=CC=NC=C1 RUIZBQQGWNBRFH-UHFFFAOYSA-N 0.000 claims description 8
• OQZGLXOADHKTDN-UHFFFAOYSA-N 1-oxidopyrimidin-1-ium Chemical class [O-][N+]1=CC=CN=C1 OQZGLXOADHKTDN-UHFFFAOYSA-N 0.000 claims description 8
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
• 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 8
• 238000002360 preparation method Methods 0.000 claims description 8
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000005237 alkyleneamino group Chemical group 0.000 claims description 7
• 125000003700 epoxy group Chemical group 0.000 claims description 7
• 230000003287 optical effect Effects 0.000 claims description 7
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
• 125000006177 alkyl benzyl group Chemical group 0.000 claims description 6
• 125000005336 allyloxy group Chemical group 0.000 claims description 6
• 239000007795 chemical reaction product Substances 0.000 claims description 6
• 125000006277 halobenzyl group Chemical group 0.000 claims description 6
• 150000004678 hydrides Chemical class 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
• 238000003797 solvolysis reaction Methods 0.000 claims description 6
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
• 125000000068 chlorophenyl group Chemical group 0.000 claims description 5
• 238000009833 condensation Methods 0.000 claims description 5
• 230000005494 condensation Effects 0.000 claims description 5
• 230000003301 hydrolyzing effect Effects 0.000 claims description 5
• 229910052751 metal Inorganic materials 0.000 claims description 5
• 239000002184 metal Substances 0.000 claims description 5
• 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 5
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
• 125000006307 alkoxy benzyl group Chemical group 0.000 claims description 4
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 4
• 150000003973 alkyl amines Chemical class 0.000 claims description 4
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
• 125000000623 heterocyclic group Chemical group 0.000 claims description 4
• 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 4
• 125000006493 trifluoromethyl benzyl group Chemical group 0.000 claims description 4
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
• 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 3
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
• 238000005915 ammonolysis reaction Methods 0.000 claims description 3
• 150000003935 benzaldehydes Chemical class 0.000 claims description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• 239000012876 carrier material Substances 0.000 claims description 3
• 125000005059 halophenyl group Chemical group 0.000 claims description 3
• UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 3
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 3
• LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 2
• 101150052863 THY1 gene Proteins 0.000 claims description 2
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 2
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 claims description 2
• 239000003638 chemical reducing agent Substances 0.000 claims description 2
• NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 2
• 239000000543 intermediate Substances 0.000 claims description 2
• 125000004429 atom Chemical group 0.000 claims 4
• 125000001589 carboacyl group Chemical group 0.000 claims 4
• 239000010985 leather Substances 0.000 claims 4
• 125000006361 alkylene amino carbonyl group Chemical group 0.000 claims 2
• 125000005505 thiomorpholino group Chemical group 0.000 claims 2
• NIIPNAJXERMYOG-UHFFFAOYSA-N 1,1,2-trimethylhydrazine Chemical compound CNN(C)C NIIPNAJXERMYOG-UHFFFAOYSA-N 0.000 claims 1
• GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 claims 1
• 125000002009 alkene group Chemical group 0.000 claims 1
• 125000005082 alkoxyalkenyl group Chemical group 0.000 claims 1
• 125000004848 alkoxyethyl group Chemical group 0.000 claims 1
• LTXJLQINBYSQFU-UHFFFAOYSA-N pyrimidin-5-ol Chemical compound OC1=CN=CN=C1 LTXJLQINBYSQFU-UHFFFAOYSA-N 0.000 claims 1
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 171
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 126
• 239000000243 solution Substances 0.000 description 126
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 100
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 69
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 66
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 53
• 239000003921 oil Substances 0.000 description 52
• 235000019198 oils Nutrition 0.000 description 52
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 49
• 239000011541 reaction mixture Substances 0.000 description 45
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 44
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 38
• 235000011121 sodium hydroxide Nutrition 0.000 description 38
• 239000002904 solvent Substances 0.000 description 35
• 238000003756 stirring Methods 0.000 description 34
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 32
• 229910052938 sodium sulfate Inorganic materials 0.000 description 32
• 235000011152 sodium sulphate Nutrition 0.000 description 32
• 238000001704 evaporation Methods 0.000 description 31
• 238000002844 melting Methods 0.000 description 31
• 230000008018 melting Effects 0.000 description 31
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 30
• 230000008020 evaporation Effects 0.000 description 30
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 28
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 27
• 239000000155 melt Substances 0.000 description 27
• 229910000104 sodium hydride Inorganic materials 0.000 description 27
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 26
• 238000009835 boiling Methods 0.000 description 26
• 239000012312 sodium hydride Substances 0.000 description 26
• 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 description 25
• 239000000725 suspension Substances 0.000 description 25
• 239000000706 filtrate Substances 0.000 description 23
• 230000007935 neutral effect Effects 0.000 description 23
• 239000008346 aqueous phase Substances 0.000 description 22
• 229960004592 isopropanol Drugs 0.000 description 22
• 239000001530 fumaric acid Substances 0.000 description 21
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 21
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 20
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
• 239000003054 catalyst Substances 0.000 description 19
• 239000000284 extract Substances 0.000 description 18
• 238000001035 drying Methods 0.000 description 17
• 239000012259 ether extract Substances 0.000 description 17
• 230000002378 acidificating effect Effects 0.000 description 16
• 238000001816 cooling Methods 0.000 description 16
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 16
• 238000010992 reflux Methods 0.000 description 16
• 239000007868 Raney catalyst Substances 0.000 description 14
• 229910000564 Raney nickel Inorganic materials 0.000 description 14
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
• 150000007513 acids Chemical class 0.000 description 14
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 14
• 238000001953 recrystallisation Methods 0.000 description 14
• NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 13
• 235000011118 potassium hydroxide Nutrition 0.000 description 13
• 239000011734 sodium Substances 0.000 description 13
• HNOAXSVPMXZKBT-UHFFFAOYSA-N (2-phenyl-3-propan-2-yl-1,3-oxazolidin-5-yl)methanol Chemical compound CC(C)N1CC(CO)OC1C1=CC=CC=C1 HNOAXSVPMXZKBT-UHFFFAOYSA-N 0.000 description 12
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 12
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
• 239000012071 phase Substances 0.000 description 12
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 12
• 229910052708 sodium Inorganic materials 0.000 description 12
• CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 11
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 11
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 11
• 150000001340 alkali metals Chemical class 0.000 description 11
• 150000002148 esters Chemical class 0.000 description 11
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 11
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
• 102000012740 beta Adrenergic Receptors Human genes 0.000 description 10
• 108010079452 beta Adrenergic Receptors Proteins 0.000 description 10
• 238000004821 distillation Methods 0.000 description 10
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
• 229910000027 potassium carbonate Inorganic materials 0.000 description 10
• 235000011181 potassium carbonates Nutrition 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 9
• 125000003118 aryl group Chemical group 0.000 description 9
• 239000013078 crystal Substances 0.000 description 9
• 239000005457 ice water Substances 0.000 description 9
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
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