TW200406413A - Compounds - Google Patents

Info

Publication number

TW200406413A

TW200406413A TW092117044A TW92117044A TW200406413A TW 200406413 A TW200406413 A TW 200406413A TW 092117044 A TW092117044 A TW 092117044A TW 92117044 A TW92117044 A TW 92117044A TW 200406413 A TW200406413 A TW 200406413A

Authority

TW

Taiwan

Prior art keywords

group

alkyl

amine

dihydro

substituted

Prior art date

2002-06-26

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims description 215
• 238000000034 method Methods 0.000 claims abstract description 164
• 208000035143 Bacterial infection Diseases 0.000 claims abstract description 6
• 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 6
• 241000124008 Mammalia Species 0.000 claims abstract description 4
• -1 Hexahydropyridyl Chemical group 0.000 claims description 220
• 125000000217 alkyl group Chemical group 0.000 claims description 203
• 150000001412 amines Chemical class 0.000 claims description 128
• 239000000203 mixture Substances 0.000 claims description 115
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 72
• 125000003277 amino group Chemical group 0.000 claims description 70
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 68
• 239000002253 acid Substances 0.000 claims description 67
• 125000003118 aryl group Chemical group 0.000 claims description 56
• 150000002367 halogens Chemical class 0.000 claims description 51
• 125000003342 alkenyl group Chemical group 0.000 claims description 50
• 230000002079 cooperative effect Effects 0.000 claims description 50
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 47
• 229910052736 halogen Inorganic materials 0.000 claims description 47
• 229910052739 hydrogen Inorganic materials 0.000 claims description 47
• 239000001257 hydrogen Substances 0.000 claims description 46
• 239000000126 substance Substances 0.000 claims description 46
• 125000003545 alkoxy group Chemical group 0.000 claims description 45
• 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 42
• 230000000875 corresponding effect Effects 0.000 claims description 41
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 37
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 35
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 33
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
• 125000000623 heterocyclic group Chemical group 0.000 claims description 24
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 23
• 150000001409 amidines Chemical class 0.000 claims description 23
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 22
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 22
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 21
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 20
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 19
• NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 19
• 125000004429 atom Chemical group 0.000 claims description 18
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 17
• 125000004414 alkyl thio group Chemical group 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 16
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
• 125000005605 benzo group Chemical group 0.000 claims description 15
• 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 125000000304 alkynyl group Chemical group 0.000 claims description 12
• 125000000468 ketone group Chemical group 0.000 claims description 12
• HIZVCIIORGCREW-UHFFFAOYSA-N 1,4-dioxene Chemical compound C1COC=CO1 HIZVCIIORGCREW-UHFFFAOYSA-N 0.000 claims description 11
• 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
• 101100240517 Caenorhabditis elegans nhr-11 gene Proteins 0.000 claims description 10
• 125000006574 non-aromatic ring group Chemical group 0.000 claims description 10
• 150000003254 radicals Chemical class 0.000 claims description 10
• 101150020251 NR13 gene Proteins 0.000 claims description 9
• VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims description 9
• 239000011737 fluorine Chemical group 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 9
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
• 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 9
• BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 9
• 238000006467 substitution reaction Methods 0.000 claims description 8
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• 125000005843 halogen group Chemical group 0.000 claims description 7
• 125000005647 linker group Chemical group 0.000 claims description 7
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• CYSPWCARDHRYJX-UHFFFAOYSA-N 9h-fluoren-1-amine Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2N CYSPWCARDHRYJX-UHFFFAOYSA-N 0.000 claims description 6
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
• 229930194542 Keto Natural products 0.000 claims description 5
• 241000981595 Zoysia japonica Species 0.000 claims description 5
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
• 125000003282 alkyl amino group Chemical group 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 5
• 125000005429 oxyalkyl group Chemical group 0.000 claims description 5
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
• 229910052721 tungsten Inorganic materials 0.000 claims description 5
• HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims description 4
• 101000585507 Solanum tuberosum Cytochrome b-c1 complex subunit 7 Proteins 0.000 claims description 4
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
• 125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 4
• 125000003368 amide group Chemical group 0.000 claims description 4
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
• 235000012149 noodles Nutrition 0.000 claims description 4
• 229920002554 vinyl polymer Polymers 0.000 claims description 4
• 229910052727 yttrium Inorganic materials 0.000 claims description 4
• 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 3
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 3
• 150000004820 halides Chemical class 0.000 claims description 3
• 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 claims description 3
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
• 125000006413 ring segment Chemical group 0.000 claims description 3
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims description 3
• VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 claims description 2
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
• 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims description 2
• WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 2
• 241000283074 Equus asinus Species 0.000 claims description 2
• 229910000831 Steel Inorganic materials 0.000 claims description 2
• 125000005110 aryl thio group Chemical group 0.000 claims description 2
• 125000004104 aryloxy group Chemical group 0.000 claims description 2
• 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 2
• 229910052796 boron Inorganic materials 0.000 claims description 2
• 210000004268 dentin Anatomy 0.000 claims description 2
• 229940079593 drug Drugs 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
• 125000004468 heterocyclylthio group Chemical group 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
• 239000010959 steel Substances 0.000 claims description 2
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 4
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 4
• RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 3
• 125000004432 carbon atom Chemical group C* 0.000 claims 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• WGJTWWOOHRIOBI-UHFFFAOYSA-N 1-(9H-fluoren-3-yl)-9H-fluorene Chemical compound C1C2=CC=CC=C2C2=C1C(C=1C=C3C4=CC=CC=C4CC3=CC=1)=CC=C2 WGJTWWOOHRIOBI-UHFFFAOYSA-N 0.000 claims 1
• APWAMQGDVJNMRK-UHFFFAOYSA-N 2-methoxy-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(OC)C=C3CC2=C1 APWAMQGDVJNMRK-UHFFFAOYSA-N 0.000 claims 1
• 101100021281 Caenorhabditis elegans lin-8 gene Proteins 0.000 claims 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
• 125000002877 alkyl aryl group Chemical group 0.000 claims 1
• 125000005360 alkyl sulfoxide group Chemical group 0.000 claims 1
• 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
• GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims 1
• 125000001589 carboacyl group Chemical group 0.000 claims 1
• 235000013365 dairy product Nutrition 0.000 claims 1
• 238000010586 diagram Methods 0.000 claims 1
• 235000001916 dieting Nutrition 0.000 claims 1
• 230000037228 dieting effect Effects 0.000 claims 1
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 1
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
• JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 claims 1
• BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical group [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims 1
• 229910052716 thallium Inorganic materials 0.000 claims 1
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
• 125000000596 cyclohexenyl group Chemical class C1(=CCCCC1)* 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 195
• 239000007787 solid Substances 0.000 description 183
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 157
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 126
• 239000000243 solution Substances 0.000 description 126
• 150000002500 ions Chemical class 0.000 description 123
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 93
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
• 238000006243 chemical reaction Methods 0.000 description 72
• 239000007921 spray Substances 0.000 description 72
• 150000001299 aldehydes Chemical class 0.000 description 70
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 58
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
• 229910001868 water Inorganic materials 0.000 description 53
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
• 230000008569 process Effects 0.000 description 51
• 235000019439 ethyl acetate Nutrition 0.000 description 48
• 238000005507 spraying Methods 0.000 description 43
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 38
• 239000002585 base Substances 0.000 description 37
• 238000013375 chromatographic separation Methods 0.000 description 37
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 33
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 31
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
• 101150041968 CDC13 gene Proteins 0.000 description 29
• 239000012458 free base Substances 0.000 description 29
• 239000003921 oil Substances 0.000 description 29
• 235000019198 oils Nutrition 0.000 description 29
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 28
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
• 239000000741 silica gel Substances 0.000 description 28
• 229910002027 silica gel Inorganic materials 0.000 description 28
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
• 239000000284 extract Substances 0.000 description 27
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 26
• 150000002148 esters Chemical class 0.000 description 25
• 238000004519 manufacturing process Methods 0.000 description 25
• 239000000463 material Substances 0.000 description 23
• 239000000047 product Substances 0.000 description 22
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
• 150000003839 salts Chemical class 0.000 description 19
• 238000005932 reductive alkylation reaction Methods 0.000 description 18
• 229920006395 saturated elastomer Polymers 0.000 description 18
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 17
• 239000002904 solvent Substances 0.000 description 17
• 238000003756 stirring Methods 0.000 description 17
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 16
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
• 239000010410 layer Substances 0.000 description 15
• 238000006722 reduction reaction Methods 0.000 description 15
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 15
• 229910052786 argon Inorganic materials 0.000 description 14
• 239000003153 chemical reaction reagent Substances 0.000 description 14
• 238000007796 conventional method Methods 0.000 description 14
• 239000011541 reaction mixture Substances 0.000 description 14
• 230000002829 reductive effect Effects 0.000 description 14
• 238000010992 reflux Methods 0.000 description 14
• 238000000926 separation method Methods 0.000 description 14
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 14
• 238000001914 filtration Methods 0.000 description 13
• 235000017557 sodium bicarbonate Nutrition 0.000 description 13
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 12
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 12
• 238000002360 preparation method Methods 0.000 description 12
• 230000009467 reduction Effects 0.000 description 12
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
• 239000012267 brine Substances 0.000 description 11
• 230000008859 change Effects 0.000 description 11
• 239000000460 chlorine Substances 0.000 description 11
• 239000000543 intermediate Substances 0.000 description 11
• 238000012360 testing method Methods 0.000 description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
• 229910000027 potassium carbonate Inorganic materials 0.000 description 10
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 10
• 239000000052 vinegar Substances 0.000 description 10
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 9
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 9
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
• 238000001816 cooling Methods 0.000 description 9
• 230000007062 hydrolysis Effects 0.000 description 9
• 238000006460 hydrolysis reaction Methods 0.000 description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
• 239000011734 sodium Substances 0.000 description 9
• 239000012279 sodium borohydride Substances 0.000 description 9
• 229910000033 sodium borohydride Inorganic materials 0.000 description 9
• 235000021419 vinegar Nutrition 0.000 description 9
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 8
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 8
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
• 229910021529 ammonia Inorganic materials 0.000 description 8
• 150000001540 azides Chemical class 0.000 description 8
• 230000015572 biosynthetic process Effects 0.000 description 8
• 239000003638 chemical reducing agent Substances 0.000 description 8
• 238000004587 chromatography analysis Methods 0.000 description 8
• 239000000499 gel Substances 0.000 description 8
• 229910052744 lithium Inorganic materials 0.000 description 8
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
• 239000012071 phase Substances 0.000 description 8
• 235000011181 potassium carbonates Nutrition 0.000 description 8
• 229910052708 sodium Inorganic materials 0.000 description 8
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