CA1062713A - Pyrimidine derivatives - Google Patents
Pyrimidine derivativesInfo
- Publication number
- CA1062713A CA1062713A CA261,472A CA261472A CA1062713A CA 1062713 A CA1062713 A CA 1062713A CA 261472 A CA261472 A CA 261472A CA 1062713 A CA1062713 A CA 1062713A
- Authority
- CA
- Canada
- Prior art keywords
- pyrimidine
- cyanophenyl
- cyano
- straight
- carbon atoms
- Prior art date
- 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.)
- Expired
Links
- 150000003230 pyrimidines Chemical class 0.000 title claims description 49
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 95
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 55
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 27
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 26
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 165
- 239000000203 mixture Substances 0.000 claims description 93
- -1 p-n-propylbenzyliden Chemical class 0.000 claims description 90
- 238000000034 method Methods 0.000 claims description 61
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 60
- GQJHPVOLXNKXKB-UHFFFAOYSA-N 4-[5-(4-butylphenyl)pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(CCCC)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 GQJHPVOLXNKXKB-UHFFFAOYSA-N 0.000 claims description 42
- GYTQATZRVCZAKR-UHFFFAOYSA-N 4-[(4-butylphenyl)methylideneamino]benzonitrile Chemical compound C1=CC(CCCC)=CC=C1C=NC1=CC=C(C#N)C=C1 GYTQATZRVCZAKR-UHFFFAOYSA-N 0.000 claims description 31
- WNPUCDQWHSMXIN-UHFFFAOYSA-N 4-[(4-propylphenyl)methylideneamino]benzonitrile Chemical compound C1=CC(CCC)=CC=C1C=NC1=CC=C(C#N)C=C1 WNPUCDQWHSMXIN-UHFFFAOYSA-N 0.000 claims description 25
- JFKUBRAOUZEZSL-UHFFFAOYSA-N 4-butylbenzoic acid Chemical compound CCCCC1=CC=C(C(O)=O)C=C1 JFKUBRAOUZEZSL-UHFFFAOYSA-N 0.000 claims description 23
- VSNGFYYRBATOTN-UHFFFAOYSA-N 4-(5-heptylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCCCCCC)=CN=C1C1=CC=C(C#N)C=C1 VSNGFYYRBATOTN-UHFFFAOYSA-N 0.000 claims description 20
- CPEPWESLFZVUEP-UHFFFAOYSA-N 4-hexylbenzoic acid Chemical compound CCCCCCC1=CC=C(C(O)=O)C=C1 CPEPWESLFZVUEP-UHFFFAOYSA-N 0.000 claims description 19
- RGONNDWSVOCREF-UHFFFAOYSA-N 4-(5-pentylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCCCC)=CN=C1C1=CC=C(C#N)C=C1 RGONNDWSVOCREF-UHFFFAOYSA-N 0.000 claims description 15
- MOXOWUJNSDTVNT-UHFFFAOYSA-N 4-[(4-hexylphenyl)methylideneamino]benzonitrile Chemical compound C1=CC(CCCCCC)=CC=C1C=NC1=CC=C(C#N)C=C1 MOXOWUJNSDTVNT-UHFFFAOYSA-N 0.000 claims description 13
- CWYNKKGQJYAHQG-UHFFFAOYSA-N 4-pentylbenzoic acid Chemical compound CCCCCC1=CC=C(C(O)=O)C=C1 CWYNKKGQJYAHQG-UHFFFAOYSA-N 0.000 claims description 13
- JAQRHTMJENGRAT-UHFFFAOYSA-N 4-[5-(4-propylphenyl)pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(CCC)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 JAQRHTMJENGRAT-UHFFFAOYSA-N 0.000 claims description 10
- NFRZCHYTIYXFAC-UHFFFAOYSA-N 4-[4-(5-butylpyrimidin-2-yl)phenyl]benzonitrile Chemical compound N1=CC(CCCC)=CN=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 NFRZCHYTIYXFAC-UHFFFAOYSA-N 0.000 claims description 8
- YMIIURUWKBIOHR-UHFFFAOYSA-N 4-[4-(5-pentylpyrimidin-2-yl)phenyl]benzonitrile Chemical compound N1=CC(CCCCC)=CN=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 YMIIURUWKBIOHR-UHFFFAOYSA-N 0.000 claims description 8
- 125000005910 alkyl carbonate group Chemical group 0.000 claims description 8
- HHPCNRKYVYWYAU-UHFFFAOYSA-N 4-cyano-4'-pentylbiphenyl Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1 HHPCNRKYVYWYAU-UHFFFAOYSA-N 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- MAYOJSWIHDBLSY-UHFFFAOYSA-N 4-(5-hexylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCCCCC)=CN=C1C1=CC=C(C#N)C=C1 MAYOJSWIHDBLSY-UHFFFAOYSA-N 0.000 claims description 6
- HWICAQGSMHNVEO-UHFFFAOYSA-N 4-[5-(4-hexylphenyl)pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(CCCCCC)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 HWICAQGSMHNVEO-UHFFFAOYSA-N 0.000 claims description 6
- UOTHTRYPSFCSIX-UHFFFAOYSA-N 2-[4-(4-propylphenyl)phenyl]pyrimidine-5-carbonitrile Chemical compound C1=CC(CCC)=CC=C1C1=CC=C(C=2N=CC(=CN=2)C#N)C=C1 UOTHTRYPSFCSIX-UHFFFAOYSA-N 0.000 claims description 5
- VSUKEWPHURLYTK-UHFFFAOYSA-N 4-heptylbenzoic acid Chemical compound CCCCCCCC1=CC=C(C(O)=O)C=C1 VSUKEWPHURLYTK-UHFFFAOYSA-N 0.000 claims description 5
- YYXBAYZPDQVLAE-UHFFFAOYSA-N 2-(4-hexylphenyl)pyrimidine-5-carbonitrile Chemical compound C1=CC(CCCCCC)=CC=C1C1=NC=C(C#N)C=N1 YYXBAYZPDQVLAE-UHFFFAOYSA-N 0.000 claims description 4
- GLWIVEREPMYIDL-UHFFFAOYSA-N 2-[4-(4-hexylphenyl)phenyl]pyrimidine-5-carbonitrile Chemical compound C1=CC(CCCCCC)=CC=C1C1=CC=C(C=2N=CC(=CN=2)C#N)C=C1 GLWIVEREPMYIDL-UHFFFAOYSA-N 0.000 claims description 4
- RDISTOCQRJJICR-UHFFFAOYSA-N 4-(4-pentoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCC)=CC=C1C1=CC=C(C#N)C=C1 RDISTOCQRJJICR-UHFFFAOYSA-N 0.000 claims description 4
- XJLAPYRYCHYFKX-UHFFFAOYSA-N 4-[2-(4-hexylphenyl)pyrimidin-5-yl]benzonitrile Chemical compound C1=CC(CCCCCC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C#N)C=N1 XJLAPYRYCHYFKX-UHFFFAOYSA-N 0.000 claims description 4
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 4
- VWJMXUYCJCQLLY-UHFFFAOYSA-N 2-(4-pentylphenyl)pyrimidine-5-carbonitrile Chemical compound C1=CC(CCCCC)=CC=C1C1=NC=C(C#N)C=N1 VWJMXUYCJCQLLY-UHFFFAOYSA-N 0.000 claims description 3
- CYIUTEWMRFLAQG-UHFFFAOYSA-N 2-[4-(4-butylphenyl)phenyl]pyrimidine-5-carbonitrile Chemical compound C1=CC(CCCC)=CC=C1C1=CC=C(C=2N=CC(=CN=2)C#N)C=C1 CYIUTEWMRFLAQG-UHFFFAOYSA-N 0.000 claims description 3
- XWUMNFKBSYDPGC-UHFFFAOYSA-N 4-[2-(4-butylphenyl)pyrimidin-5-yl]benzonitrile Chemical compound C1=CC(CCCC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C#N)C=N1 XWUMNFKBSYDPGC-UHFFFAOYSA-N 0.000 claims description 3
- OFPINHYWQJBCGU-UHFFFAOYSA-N 4-[4-(5-hexylpyrimidin-2-yl)phenyl]benzonitrile Chemical compound N1=CC(CCCCCC)=CN=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 OFPINHYWQJBCGU-UHFFFAOYSA-N 0.000 claims description 3
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 3
- CIKMJMZDYLTXHC-UHFFFAOYSA-N 4-[2-(4-propylphenyl)pyrimidin-5-yl]benzonitrile Chemical compound C1=CC(CCC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C#N)C=N1 CIKMJMZDYLTXHC-UHFFFAOYSA-N 0.000 claims description 2
- 230000005684 electric field Effects 0.000 claims description 2
- KOJFDWLUULONAE-UHFFFAOYSA-N 4-[5-(4-pentoxyphenyl)pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(OCCCCC)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 KOJFDWLUULONAE-UHFFFAOYSA-N 0.000 claims 3
- LBFLIDCXWNVNLB-UHFFFAOYSA-N 2-(4-butoxyphenyl)pyrimidine-5-carbonitrile Chemical compound C1=CC(OCCCC)=CC=C1C1=NC=C(C#N)C=N1 LBFLIDCXWNVNLB-UHFFFAOYSA-N 0.000 claims 2
- AAGXGAXIWUSMKE-UHFFFAOYSA-N 2-[4-(4-ethylphenyl)phenyl]pyrimidine-5-carbonitrile Chemical compound C1=CC(CC)=CC=C1C1=CC=C(C=2N=CC(=CN=2)C#N)C=C1 AAGXGAXIWUSMKE-UHFFFAOYSA-N 0.000 claims 2
- CBEXHCVSJVGBCO-UHFFFAOYSA-N 4-[2-(4-heptylphenyl)pyrimidin-5-yl]benzonitrile Chemical compound C1=CC(CCCCCCC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C#N)C=N1 CBEXHCVSJVGBCO-UHFFFAOYSA-N 0.000 claims 2
- VKTWVTMDYIPLPB-UHFFFAOYSA-N 4-[2-(4-pentylphenyl)pyrimidin-5-yl]benzonitrile Chemical compound C1=CC(CCCCC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C#N)C=N1 VKTWVTMDYIPLPB-UHFFFAOYSA-N 0.000 claims 2
- VYTLMDTWWRXBIE-UHFFFAOYSA-N 4-[4-(5-heptylpyrimidin-2-yl)phenyl]benzonitrile Chemical compound N1=CC(CCCCCCC)=CN=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 VYTLMDTWWRXBIE-UHFFFAOYSA-N 0.000 claims 2
- HYXMQYSMPKFEMB-UHFFFAOYSA-N 4-[4-(5-propylpyrimidin-2-yl)phenyl]benzonitrile Chemical compound N1=CC(CCC)=CN=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 HYXMQYSMPKFEMB-UHFFFAOYSA-N 0.000 claims 2
- BHBQYMZPUNLWMH-UHFFFAOYSA-N 4-[5-(4-butoxyphenyl)pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(OCCCC)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 BHBQYMZPUNLWMH-UHFFFAOYSA-N 0.000 claims 2
- WSKUXWJOUAZQEY-UHFFFAOYSA-N 4-[5-(4-ethylphenyl)pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(CC)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 WSKUXWJOUAZQEY-UHFFFAOYSA-N 0.000 claims 2
- SHOZKBAAQMRSAY-UHFFFAOYSA-N 4-[5-(4-pentylphenyl)pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(CCCCC)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 SHOZKBAAQMRSAY-UHFFFAOYSA-N 0.000 claims 2
- KUGQSXAAQIUIDI-UHFFFAOYSA-N 4-[5-(4-propoxyphenyl)pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(OCCC)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 KUGQSXAAQIUIDI-UHFFFAOYSA-N 0.000 claims 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims 1
- XRMIFWVFLHAYPW-UHFFFAOYSA-N 4-[2-(4-ethylphenyl)pyrimidin-5-yl]benzonitrile Chemical compound C1=CC(CC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C#N)C=N1 XRMIFWVFLHAYPW-UHFFFAOYSA-N 0.000 claims 1
- ABJPSOVDZKBOCE-UHFFFAOYSA-N 4-[5-(4-heptylphenyl)pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 ABJPSOVDZKBOCE-UHFFFAOYSA-N 0.000 claims 1
- VJRJOSMTPOEQOO-UHFFFAOYSA-N 4-[5-(4-hexoxyphenyl)pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(OCCCCCC)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 VJRJOSMTPOEQOO-UHFFFAOYSA-N 0.000 claims 1
- 230000005693 optoelectronics Effects 0.000 claims 1
- 238000002844 melting Methods 0.000 description 82
- 230000008018 melting Effects 0.000 description 82
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 18
- 238000010992 reflux Methods 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- 230000007935 neutral effect Effects 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- 125000004802 cyanophenyl group Chemical group 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 230000018044 dehydration Effects 0.000 description 8
- 238000006297 dehydration reaction Methods 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- WGCKVXHOTDDNOA-UHFFFAOYSA-N 4-pyrimidin-2-ylbenzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=NC=CC=N1 WGCKVXHOTDDNOA-UHFFFAOYSA-N 0.000 description 5
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 5
- ZGOWXOZNUNZPAV-UHFFFAOYSA-N 4-(4-heptylphenyl)benzonitrile Chemical group C1=CC(CCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 ZGOWXOZNUNZPAV-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 230000007717 exclusion Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- AITQOXOBSMXBRV-UHFFFAOYSA-N 4-[4-(4-pentylphenyl)phenyl]benzonitrile Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 AITQOXOBSMXBRV-UHFFFAOYSA-N 0.000 description 3
- IYIAWOSYBLPUNL-UHFFFAOYSA-N 4-carbamimidoylbenzamide;hydrochloride Chemical compound Cl.NC(=N)C1=CC=C(C(N)=O)C=C1 IYIAWOSYBLPUNL-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 2
- JXNZECXISPFJQO-UHFFFAOYSA-N 2-(4-pentylphenyl)pyrimidine Chemical compound C1=CC(CCCCC)=CC=C1C1=NC=CC=N1 JXNZECXISPFJQO-UHFFFAOYSA-N 0.000 description 2
- QPFDPJJNUKGHBB-UHFFFAOYSA-N 2-(ethoxymethylidene)nonanal Chemical compound CCCCCCCC(C=O)=COCC QPFDPJJNUKGHBB-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 2
- BHVHKOVPWZKVCC-UHFFFAOYSA-N 4-(4-bromophenyl)benzonitrile Chemical group C1=CC(Br)=CC=C1C1=CC=C(C#N)C=C1 BHVHKOVPWZKVCC-UHFFFAOYSA-N 0.000 description 2
- DANLZOIRUUHIIX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DANLZOIRUUHIIX-UHFFFAOYSA-N 0.000 description 2
- PPKXLWZBHTYSSL-UHFFFAOYSA-N 4-hexylbenzenecarboximidamide;hydrochloride Chemical compound Cl.CCCCCCC1=CC=C(C(N)=N)C=C1 PPKXLWZBHTYSSL-UHFFFAOYSA-N 0.000 description 2
- ZQLDNJKHLQOJGE-UHFFFAOYSA-N 4-octylbenzoic acid Chemical compound CCCCCCCCC1=CC=C(C(O)=O)C=C1 ZQLDNJKHLQOJGE-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- OQIQSTLJSLGHID-WNWIJWBNSA-N aflatoxin B1 Chemical compound C=1([C@@H]2C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O OQIQSTLJSLGHID-WNWIJWBNSA-N 0.000 description 2
- MJBWDEQAUQTVKK-IAGOWNOFSA-N aflatoxin M1 Chemical compound C=1([C@]2(O)C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O MJBWDEQAUQTVKK-IAGOWNOFSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- 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 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- IFKPLJWIEQBPGG-QGZVFWFLSA-N (5s)-6-(dimethylamino)-5-methyl-4,4-diphenylhexan-3-one Chemical compound C=1C=CC=CC=1C([C@H](C)CN(C)C)(C(=O)CC)C1=CC=CC=C1 IFKPLJWIEQBPGG-QGZVFWFLSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- URJKFFKPVKAYHS-UHFFFAOYSA-N 1-hexyl-4-phenylcyclohexa-2,4-diene-1-carboximidamide hydrochloride Chemical compound Cl.C(CCCCC)C1(CC=C(C=C1)C1=CC=CC=C1)C(=N)N URJKFFKPVKAYHS-UHFFFAOYSA-N 0.000 description 1
- DJKONKMRNSRJKX-UHFFFAOYSA-N 2-(4-hexylphenyl)pyrimidine-5-carbonyl chloride Chemical compound C1=CC(CCCCCC)=CC=C1C1=NC=C(C(Cl)=O)C=N1 DJKONKMRNSRJKX-UHFFFAOYSA-N 0.000 description 1
- GNPMRDPPLWHZOG-UHFFFAOYSA-N 2-(4-hexylphenyl)pyrimidine-5-carboxamide Chemical compound C1=CC(CCCCCC)=CC=C1C1=NC=C(C(N)=O)C=N1 GNPMRDPPLWHZOG-UHFFFAOYSA-N 0.000 description 1
- FOYJDDBRGGFCCH-UHFFFAOYSA-N 2-(4-hexylphenyl)pyrimidine-5-carboxylic acid Chemical compound C1=CC(CCCCCC)=CC=C1C1=NC=C(C(O)=O)C=N1 FOYJDDBRGGFCCH-UHFFFAOYSA-N 0.000 description 1
- WCGATDWYAFXALE-UHFFFAOYSA-N 2-[(4-propylphenyl)methylideneamino]benzonitrile Chemical compound C(CC)C1=CC=C(C=NC2=C(C#N)C=CC=C2)C=C1 WCGATDWYAFXALE-UHFFFAOYSA-N 0.000 description 1
- KKGGQOYYNHQNGB-UHFFFAOYSA-N 2-[4-(4-bromophenyl)phenyl]-5-pentylpyrimidine Chemical compound N1=CC(CCCCC)=CN=C1C1=CC=C(C=2C=CC(Br)=CC=2)C=C1 KKGGQOYYNHQNGB-UHFFFAOYSA-N 0.000 description 1
- FBWWSILRZCRUAQ-UHFFFAOYSA-N 2-[4-(4-butoxyphenyl)phenyl]pyrimidine-5-carbonitrile Chemical compound C1=CC(OCCCC)=CC=C1C1=CC=C(C=2N=CC(=CN=2)C#N)C=C1 FBWWSILRZCRUAQ-UHFFFAOYSA-N 0.000 description 1
- HFYMROMZKSTMGO-UHFFFAOYSA-N 2-[4-(4-ethoxyphenyl)phenyl]pyrimidine-5-carbonitrile Chemical compound C1=CC(OCC)=CC=C1C1=CC=C(C=2N=CC(=CN=2)C#N)C=C1 HFYMROMZKSTMGO-UHFFFAOYSA-N 0.000 description 1
- JUFRJJFMFBNCEQ-UHFFFAOYSA-N 2-[4-(4-hexylphenyl)phenyl]pyrimidine-5-carboxylic acid Chemical compound C1=CC(CCCCCC)=CC=C1C1=CC=C(C=2N=CC(=CN=2)C(O)=O)C=C1 JUFRJJFMFBNCEQ-UHFFFAOYSA-N 0.000 description 1
- KENBWXYSHDOZCO-UHFFFAOYSA-N 2-[4-(4-methylphenyl)phenyl]pyrimidine-5-carbonitrile Chemical compound C1=CC(C)=CC=C1C1=CC=C(C=2N=CC(=CN=2)C#N)C=C1 KENBWXYSHDOZCO-UHFFFAOYSA-N 0.000 description 1
- MVMNCWIVJRIIKC-UHFFFAOYSA-N 2-[4-(4-pentoxyphenyl)phenyl]pyrimidine-5-carbonitrile Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC=C(C=2N=CC(=CN=2)C#N)C=C1 MVMNCWIVJRIIKC-UHFFFAOYSA-N 0.000 description 1
- QOHYUAFWDHWNEC-UHFFFAOYSA-N 2-[4-(4-pentylphenyl)phenyl]pyrimidine-5-carbonitrile Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(C=2N=CC(=CN=2)C#N)C=C1 QOHYUAFWDHWNEC-UHFFFAOYSA-N 0.000 description 1
- YNFUGQHDAKFMGG-UHFFFAOYSA-N 2-heptylbenzoic acid Chemical compound CCCCCCCC1=CC=CC=C1C(O)=O YNFUGQHDAKFMGG-UHFFFAOYSA-N 0.000 description 1
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 1
- OYOZWFXADPUJSM-UHFFFAOYSA-N 3-(4-pentylphenyl)benzonitrile Chemical group C1=CC(CCCCC)=CC=C1C1=CC=CC(C#N)=C1 OYOZWFXADPUJSM-UHFFFAOYSA-N 0.000 description 1
- CKXFRXCNDDLVAP-UHFFFAOYSA-N 3-ethoxy-2-(4-pentylphenyl)prop-2-enal Chemical compound CCCCCC1=CC=C(C(C=O)=COCC)C=C1 CKXFRXCNDDLVAP-UHFFFAOYSA-N 0.000 description 1
- JNPDFMDFQSMIMB-UHFFFAOYSA-N 3-heptoxy-4-phenylbenzonitrile Chemical group CCCCCCCOc1cc(ccc1-c1ccccc1)C#N JNPDFMDFQSMIMB-UHFFFAOYSA-N 0.000 description 1
- OHRRAMUSQRPBNH-UHFFFAOYSA-N 3-hexylbenzoic acid Chemical compound CCCCCCC1=CC=CC(C(O)=O)=C1 OHRRAMUSQRPBNH-UHFFFAOYSA-N 0.000 description 1
- SLCDMYPZGHPEPA-UHFFFAOYSA-N 3-pentyl-4-phenylbenzonitrile Chemical group CCCCCC1=CC(C#N)=CC=C1C1=CC=CC=C1 SLCDMYPZGHPEPA-UHFFFAOYSA-N 0.000 description 1
- AZDGDDGUHUQQMO-UHFFFAOYSA-N 4-(4-bromophenyl)benzaldehyde Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C=O)C=C1 AZDGDDGUHUQQMO-UHFFFAOYSA-N 0.000 description 1
- LFXGJUCNXVCZSU-UHFFFAOYSA-N 4-(4-bromophenyl)benzenecarboximidamide;hydrochloride Chemical compound Cl.C1=CC(C(=N)N)=CC=C1C1=CC=C(Br)C=C1 LFXGJUCNXVCZSU-UHFFFAOYSA-N 0.000 description 1
- GLGVASKFXIKAIA-UHFFFAOYSA-N 4-(4-heptylpyrimidin-2-yl)benzamide Chemical compound CCCCCCCC1=CC=NC(C=2C=CC(=CC=2)C(N)=O)=N1 GLGVASKFXIKAIA-UHFFFAOYSA-N 0.000 description 1
- VADSDVGLFDVIMG-UHFFFAOYSA-N 4-(4-hexylphenyl)benzonitrile Chemical group C1=CC(CCCCCC)=CC=C1C1=CC=C(C#N)C=C1 VADSDVGLFDVIMG-UHFFFAOYSA-N 0.000 description 1
- YFZISFITJTVAET-UHFFFAOYSA-N 4-[(4-ethoxyphenyl)methylideneamino]benzonitrile Chemical compound C1=CC(OCC)=CC=C1C=NC1=CC=C(C#N)C=C1 YFZISFITJTVAET-UHFFFAOYSA-N 0.000 description 1
- FCQPUXSTFWFVHK-UHFFFAOYSA-N 4-[(4-pentylphenyl)methylideneamino]benzonitrile Chemical compound C1=CC(CCCCC)=CC=C1C=NC1=CC=C(C#N)C=C1 FCQPUXSTFWFVHK-UHFFFAOYSA-N 0.000 description 1
- KVCZCSWIUSILAH-UHFFFAOYSA-N 4-[2-(4-methoxyphenyl)pyrimidin-5-yl]benzonitrile Chemical compound C1=CC(OC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C#N)C=N1 KVCZCSWIUSILAH-UHFFFAOYSA-N 0.000 description 1
- MVYDVOCPNTVBNU-UHFFFAOYSA-N 4-[2-(4-methylphenyl)pyrimidin-5-yl]benzonitrile Chemical compound C1=CC(C)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C#N)C=N1 MVYDVOCPNTVBNU-UHFFFAOYSA-N 0.000 description 1
- VSFYJWLBSXJCCW-UHFFFAOYSA-N 4-[2-(4-propoxyphenyl)pyrimidin-5-yl]benzonitrile Chemical compound C1=CC(OCCC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C#N)C=N1 VSFYJWLBSXJCCW-UHFFFAOYSA-N 0.000 description 1
- NFBDLNNGMUYKPV-UHFFFAOYSA-N 4-[4-(2-butylpyrimidin-5-yl)phenyl]benzonitrile Chemical compound C1=NC(CCCC)=NC=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 NFBDLNNGMUYKPV-UHFFFAOYSA-N 0.000 description 1
- GIFUOGAJLFDRBK-UHFFFAOYSA-N 4-[4-(2-ethoxypyrimidin-5-yl)phenyl]benzonitrile Chemical compound C1=NC(OCC)=NC=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 GIFUOGAJLFDRBK-UHFFFAOYSA-N 0.000 description 1
- ZBMLGSXGZMDKEK-UHFFFAOYSA-N 4-[4-(2-methoxypyrimidin-5-yl)phenyl]benzonitrile Chemical compound C1=NC(OC)=NC=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 ZBMLGSXGZMDKEK-UHFFFAOYSA-N 0.000 description 1
- XSVCKGJYIDUBMX-UHFFFAOYSA-N 4-[4-(5-ethylpyrimidin-2-yl)phenyl]benzonitrile Chemical compound N1=CC(CC)=CN=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 XSVCKGJYIDUBMX-UHFFFAOYSA-N 0.000 description 1
- HQZXISDFAXSUNJ-UHFFFAOYSA-N 4-[4-(5-methoxypyrimidin-2-yl)phenyl]benzonitrile Chemical compound N1=CC(OC)=CN=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 HQZXISDFAXSUNJ-UHFFFAOYSA-N 0.000 description 1
- UEJQTDPDKTXLTQ-UHFFFAOYSA-N 4-[4-(5-methylpyrimidin-2-yl)phenyl]benzonitrile Chemical compound N1=CC(C)=CN=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 UEJQTDPDKTXLTQ-UHFFFAOYSA-N 0.000 description 1
- ARCUQACBEQIKBV-UHFFFAOYSA-N 4-[5-(4-ethoxyphenyl)pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(OCC)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 ARCUQACBEQIKBV-UHFFFAOYSA-N 0.000 description 1
- HKMIWYWBIYCXFQ-UHFFFAOYSA-N 4-carbamimidoylbenzamide Chemical compound NC(=N)C1=CC=C(C(N)=O)C=C1 HKMIWYWBIYCXFQ-UHFFFAOYSA-N 0.000 description 1
- BPMBNLJJRKCCRT-UHFFFAOYSA-N 4-phenylbenzonitrile Chemical group C1=CC(C#N)=CC=C1C1=CC=CC=C1 BPMBNLJJRKCCRT-UHFFFAOYSA-N 0.000 description 1
- KGBKQWZOVQOSRB-UHFFFAOYSA-N 5-(4-bromophenyl)-2-(4-hexylphenyl)pyrimidine Chemical compound C1=CC(CCCCCC)=CC=C1C1=NC=C(C=2C=CC(Br)=CC=2)C=N1 KGBKQWZOVQOSRB-UHFFFAOYSA-N 0.000 description 1
- GIINIYQSXNJFMJ-UHFFFAOYSA-N 5-(4-butylphenyl)pyrimidine Chemical compound C(CCC)C1=CC=C(C=C1)C=1C=NC=NC=1 GIINIYQSXNJFMJ-UHFFFAOYSA-N 0.000 description 1
- BXMWTZSHGOOMNO-UHFFFAOYSA-N 5-(4-ethylphenyl)pyrimidine Chemical compound C1=CC(CC)=CC=C1C1=CN=CN=C1 BXMWTZSHGOOMNO-UHFFFAOYSA-N 0.000 description 1
- IGTABDBDIRHVQW-UHFFFAOYSA-N 5-[4-(4-butylphenyl)phenyl]pyrimidine-2-carbonitrile Chemical compound C1=CC(CCCC)=CC=C1C1=CC=C(C=2C=NC(=NC=2)C#N)C=C1 IGTABDBDIRHVQW-UHFFFAOYSA-N 0.000 description 1
- NVFLCEAUBOKARM-UHFFFAOYSA-N 5-[4-(4-hexylphenyl)phenyl]pyrimidine-2-carbonitrile Chemical compound C1=CC(CCCCCC)=CC=C1C1=CC=C(C=2C=NC(=NC=2)C#N)C=C1 NVFLCEAUBOKARM-UHFFFAOYSA-N 0.000 description 1
- SLMPUGJFDMZQEJ-UHFFFAOYSA-N 5-[4-(4-pentoxyphenyl)phenyl]pyrimidine-2-carbonitrile Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC=C(C=2C=NC(=NC=2)C#N)C=C1 SLMPUGJFDMZQEJ-UHFFFAOYSA-N 0.000 description 1
- FNEHIQSUQDWRAK-UHFFFAOYSA-N 5-[4-(4-propoxyphenyl)phenyl]pyrimidine-2-carbonitrile Chemical compound C1=CC(OCCC)=CC=C1C1=CC=C(C=2C=NC(=NC=2)C#N)C=C1 FNEHIQSUQDWRAK-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 244000228957 Ferula foetida Species 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 229910019201 POBr3 Inorganic materials 0.000 description 1
- 241001474977 Palla Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 101100162169 Xenopus laevis adrm1-a gene Proteins 0.000 description 1
- KIUBIHVGOSDLEB-UHFFFAOYSA-N [2-[4-(4-cyanophenyl)phenyl]pyrimidin-5-yl] heptanoate Chemical compound N1=CC(OC(=O)CCCCCC)=CN=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 KIUBIHVGOSDLEB-UHFFFAOYSA-N 0.000 description 1
- SGIVRFPNHVHOHW-UHFFFAOYSA-N [4-[2-(4-cyanophenyl)pyrimidin-5-yl]phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 SGIVRFPNHVHOHW-UHFFFAOYSA-N 0.000 description 1
- SAFPXCKDFRLJID-UHFFFAOYSA-N [4-[2-(4-cyanophenyl)pyrimidin-5-yl]phenyl] hexanoate Chemical compound C1=CC(OC(=O)CCCCC)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 SAFPXCKDFRLJID-UHFFFAOYSA-N 0.000 description 1
- XGPOTKYONGYPBR-UHFFFAOYSA-N [4-[4-(2-cyanopyrimidin-5-yl)phenyl]phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C1=CC=C(C=2C=NC(=NC=2)C#N)C=C1 XGPOTKYONGYPBR-UHFFFAOYSA-N 0.000 description 1
- ZLOJMVOKJNELOH-UHFFFAOYSA-N [4-[4-(2-cyanopyrimidin-5-yl)phenyl]phenyl] hexanoate Chemical compound C1=CC(OC(=O)CCCCC)=CC=C1C1=CC=C(C=2C=NC(=NC=2)C#N)C=C1 ZLOJMVOKJNELOH-UHFFFAOYSA-N 0.000 description 1
- CQHBTQVGNNDDAM-UHFFFAOYSA-N [4-[4-(5-cyanopyrimidin-2-yl)phenyl]phenyl] heptanoate Chemical compound C1=CC(OC(=O)CCCCCC)=CC=C1C1=CC=C(C=2N=CC(=CN=2)C#N)C=C1 CQHBTQVGNNDDAM-UHFFFAOYSA-N 0.000 description 1
- BZJQIGJFHORSTH-UHFFFAOYSA-N [4-[5-(4-cyanophenyl)pyrimidin-2-yl]phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C#N)C=N1 BZJQIGJFHORSTH-UHFFFAOYSA-N 0.000 description 1
- VVXHQJQOYZNJGL-UHFFFAOYSA-N [4-[5-(4-cyanophenyl)pyrimidin-2-yl]phenyl] heptanoate Chemical compound C1=CC(OC(=O)CCCCCC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C#N)C=N1 VVXHQJQOYZNJGL-UHFFFAOYSA-N 0.000 description 1
- DTJKVBMTFLIHOK-UHFFFAOYSA-N [5-[4-(4-cyanophenyl)phenyl]pyrimidin-2-yl] hexanoate Chemical compound C1=NC(OC(=O)CCCCC)=NC=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 DTJKVBMTFLIHOK-UHFFFAOYSA-N 0.000 description 1
- YQLMHXJICJZZFV-UHFFFAOYSA-N [amino-(4-ethoxycarbonylphenyl)methylidene]azanium;chloride Chemical compound [Cl-].CCOC(=O)C1=CC=C(C([NH3+])=N)C=C1 YQLMHXJICJZZFV-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- XJKKCLQTZOSEDY-UHFFFAOYSA-N cyano benzoate Chemical compound N#COC(=O)C1=CC=CC=C1 XJKKCLQTZOSEDY-UHFFFAOYSA-N 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- GRTGGSXWHGKRSB-UHFFFAOYSA-N dichloromethyl methyl ether Chemical compound COC(Cl)Cl GRTGGSXWHGKRSB-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
- GSKKUNWSLARPQW-UHFFFAOYSA-N ethyl 2-(4-hexylphenyl)-6-oxo-1h-pyrimidine-5-carboxylate Chemical compound C1=CC(CCCCCC)=CC=C1C1=NC=C(C(=O)OCC)C(=O)N1 GSKKUNWSLARPQW-UHFFFAOYSA-N 0.000 description 1
- WCWKDFYCCBAYIX-UHFFFAOYSA-N ethyl 2-(4-hexylphenyl)pyrimidine-5-carboxylate Chemical compound C1=CC(CCCCCC)=CC=C1C1=NC=C(C(=O)OCC)C=N1 WCWKDFYCCBAYIX-UHFFFAOYSA-N 0.000 description 1
- ZIQXJIMFEAGQGX-UHFFFAOYSA-N ethyl 2-[4-(4-hexylphenyl)phenyl]-6-oxo-1h-pyrimidine-5-carboxylate Chemical compound C1=CC(CCCCCC)=CC=C1C1=CC=C(C=2NC(=O)C(C(=O)OCC)=CN=2)C=C1 ZIQXJIMFEAGQGX-UHFFFAOYSA-N 0.000 description 1
- OPYDNRJUYMQSTE-UHFFFAOYSA-N ethyl 2-[4-(4-hexylphenyl)phenyl]pyrimidine-5-carboxylate Chemical compound C1=CC(CCCCCC)=CC=C1C1=CC=C(C=2N=CC(=CN=2)C(=O)OCC)C=C1 OPYDNRJUYMQSTE-UHFFFAOYSA-N 0.000 description 1
- UTUVEIXBMWKTLV-UHFFFAOYSA-N ethyl 4-(4-heptylpyrimidin-2-yl)benzoate Chemical compound CCCCCCCC1=CC=NC(C=2C=CC(=CC=2)C(=O)OCC)=N1 UTUVEIXBMWKTLV-UHFFFAOYSA-N 0.000 description 1
- PUCFOIDMWPCTFC-UHFFFAOYSA-N ethyl 6-oxo-2-(4-pentylphenyl)-1h-pyrimidine-5-carboxylate Chemical compound C1=CC(CCCCC)=CC=C1C1=NC=C(C(=O)OCC)C(O)=N1 PUCFOIDMWPCTFC-UHFFFAOYSA-N 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229930184652 p-Terphenyl Natural products 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- IIVUJUOJERNGQX-UHFFFAOYSA-N pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=CN=C1 IIVUJUOJERNGQX-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical class OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1223575A CH622548A5 (en) | 1975-09-19 | 1975-09-19 | Liquid-crystal mixtures |
| CH22176 | 1976-01-09 | ||
| CH231776 | 1976-02-25 | ||
| CH976176 | 1976-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1062713A true CA1062713A (en) | 1979-09-18 |
Family
ID=27427800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA261,472A Expired CA1062713A (en) | 1975-09-19 | 1976-09-17 | Pyrimidine derivatives |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4062798A (enExample) |
| JP (1) | JPS5239685A (enExample) |
| AT (1) | AT356111B (enExample) |
| CA (1) | CA1062713A (enExample) |
| DD (2) | DD135624A5 (enExample) |
| DE (1) | DE2641724C2 (enExample) |
| DK (1) | DK422376A (enExample) |
| FR (1) | FR2324636A1 (enExample) |
| GB (1) | GB1510090A (enExample) |
| HK (1) | HK2179A (enExample) |
| IL (1) | IL50478A (enExample) |
| IT (1) | IT1068298B (enExample) |
| NO (1) | NO763188L (enExample) |
| SE (1) | SE7610422L (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7701750A (nl) * | 1976-02-26 | 1977-08-30 | Hoffmann La Roche | Mengsels van vloeibare kristallen. |
| NL7801718A (nl) * | 1977-03-18 | 1978-09-20 | Hoffmann La Roche | Optische actieve verbindingen. |
| DE2815860A1 (de) * | 1977-04-15 | 1978-10-19 | Hoffmann La Roche | Fluessigkristalline mischungen |
| US4198130A (en) * | 1977-06-03 | 1980-04-15 | Hoffmann-La Roche Inc. | Liquid crystal mixtures |
| US4253740A (en) * | 1977-09-12 | 1981-03-03 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Liquid crystal materials and devices containing them |
| JPS5941983B2 (ja) * | 1978-02-17 | 1984-10-11 | 大日本インキ化学工業株式会社 | トランス（エカトリアル↓−エカトリアル）１，４↓−ジ置換シクロヘキサン誘導体 |
| US4309539A (en) * | 1978-03-13 | 1982-01-05 | Hoffmann-La Roche Inc. | Pyrimidine derivatives |
| DE2944905A1 (de) * | 1978-12-13 | 1980-10-23 | Werk Fernsehelektronik Veb | Kristallin-fluessige substituierte 1,3-dioxane und diese enthaltende gemische |
| CA1120478A (en) * | 1979-02-05 | 1982-03-23 | Arthur Boller | Cyclohexyl pyrimidines |
| DE3014912A1 (de) * | 1979-05-15 | 1980-11-27 | Werk Fernsehelektronik Veb | Nematische fluessigkristalline 5-cyan- 2- eckige klammer auf 4-acyloxyphenyl eckige klammer zu -pyrimidine und diese enthaltende gemische |
| EP0025119B1 (de) * | 1979-08-20 | 1983-05-25 | VEB Werk Für Fernsehelektronik im VEB Kombinat Mikroelektronik | Nematische kristallin-flüssige 5-Alkyl-2-(4-acyloxyphenyl)-pyrimidine für optoelektronische Anordnungen und Verfahren zu ihrer Herstellung |
| US4364838A (en) * | 1979-11-14 | 1982-12-21 | Hoffmann-La Roche Inc. | Liquid crystal mixtures |
| DE2951099A1 (de) * | 1979-12-19 | 1981-06-25 | Merck Patent Gmbh, 6100 Darmstadt | Tetrahydrochinazoline, verfahren zu ihrer herstellung, diese enthaltende fluessigkristalline dielektrika und elektrooptisches anzeigeelement |
| CH645102A5 (de) * | 1980-10-14 | 1984-09-14 | Hoffmann La Roche | Disubstituierte pyrimidine. |
| US4325830A (en) * | 1980-12-24 | 1982-04-20 | Timex Corporation | Three ring dioxane liquid crystalline compounds |
| DE3201721A1 (de) * | 1981-01-30 | 1982-08-19 | F. Hoffmann-La Roche & Co. AG, 4002 Basel | Disubstituierte aethane |
| CH651025A5 (de) * | 1982-05-14 | 1985-08-30 | Hoffmann La Roche | Pyridazine und ihre verwendung als komponenten fluessigkristalliner gemische. |
| US4452718A (en) * | 1981-07-31 | 1984-06-05 | Hoffmann-La Roche Inc. | Pyridazines |
| US4528114A (en) * | 1981-12-18 | 1985-07-09 | Hoffmann-La Roche Inc. | Acetylenes |
| US5227484A (en) * | 1982-01-14 | 1993-07-13 | Merck Patent Gmbh | Anisotropic compounds having nematic phase and liquid crystal mixtures |
| US4512636A (en) * | 1982-06-15 | 1985-04-23 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdon Of Great Britian And Northern Ireland Of Whitehall | Liquid crystal compounds |
| JPS5939876A (ja) * | 1982-08-26 | 1984-03-05 | Chisso Corp | ピリミジン誘導体 |
| DE3368618D1 (en) * | 1982-11-04 | 1987-02-05 | Ici Plc | Process for the extraction of metal values and novel metal extractants |
| EP0122389B1 (de) * | 1983-03-16 | 1987-08-05 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Flüssigkristallkomponenten mit einer Alkenylseitenkette |
| US4581155A (en) * | 1983-03-31 | 1986-04-08 | Chisso Corporation | Halogenopyrimidine derivatives |
| JPS59216876A (ja) * | 1983-05-24 | 1984-12-06 | Chisso Corp | フルオロピリミジン誘導体 |
| DE3315295A1 (de) * | 1983-04-27 | 1984-10-31 | Merck Patent Gmbh, 6100 Darmstadt | Fluorhaltige pyrimidinderivate |
| JPS60146877A (ja) * | 1984-01-11 | 1985-08-02 | Chisso Corp | ２―置換―６―（５―置換―２―ピリミジニル）ナフタリン |
| DE3401321A1 (de) * | 1984-01-17 | 1985-07-25 | Merck Patent Gmbh, 6100 Darmstadt | Stickstoffhaltige heterocyclen |
| DE3404116A1 (de) * | 1984-02-07 | 1985-08-08 | Merck Patent Gmbh, 6100 Darmstadt | Stickstoffhaltige heterocyclen |
| US4609485A (en) * | 1984-02-17 | 1986-09-02 | Chisso Corporation | Bipyrimidinyl derivatives |
| JPS61152659A (ja) * | 1984-12-27 | 1986-07-11 | Chisso Corp | １，４−ジピリミジニルベンゼン誘導体 |
| JPS61180775A (ja) * | 1985-01-22 | 1986-08-13 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | ジヒドロアジン液晶化合物 |
| JPS61197563A (ja) * | 1985-02-27 | 1986-09-01 | Chisso Corp | トリフルオロメチルフエニル基をもつピリミジン誘導体 |
| JPS61233689A (ja) * | 1985-03-22 | 1986-10-17 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | 複素環式ホウ素化合物 |
| EP0195974B1 (de) * | 1985-03-26 | 1989-11-29 | F. Hoffmann-La Roche Ag | Alkenylsubstituierte Phenylisothiocyanate und Benzonitrile |
| US4874546A (en) * | 1985-05-15 | 1989-10-17 | Chisso Corporation | Phenylpyrimidinecarboxylate derivative |
| JPS61280489A (ja) * | 1985-06-05 | 1986-12-11 | Chisso Corp | 新規液晶化合物 |
| EP0289270B1 (en) * | 1987-04-27 | 1994-12-14 | Chisso Corporation | Optically active 2-biphenylpyrimidine derivatives and liquid crystal compositions containing them |
| DE3884347T2 (de) * | 1987-11-17 | 1994-04-28 | Seiko Epson Corp | Pyrimidinderivate. |
| DE3928267A1 (de) * | 1989-08-26 | 1991-02-28 | Merck Patent Gmbh | 5-oxy-2-phenylpyrimidine und fluessigkristallines medium |
| DE4423098A1 (de) | 1994-07-01 | 1996-01-04 | Hoechst Ag | Verwendung von Pyrimidingruppen enthaltenden konjugierten Verbindungen als Elektrolumineszenzmaterialien |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1452826A (en) * | 1973-10-17 | 1976-10-20 | Secr Defence | Liquid crystal compositions |
| GB1433130A (en) * | 1972-11-09 | 1976-04-22 | Secr Defence | Substituted biphenyl and polyphenyl compounds and liquid crystal materials and devices containing them |
| DD107563A1 (enExample) * | 1973-09-27 | 1974-08-05 | ||
| CH617452A5 (enExample) * | 1974-10-25 | 1980-05-30 | Hoffmann La Roche |
-
1976
- 1976-08-30 US US05/719,018 patent/US4062798A/en not_active Expired - Lifetime
- 1976-09-13 IL IL50478A patent/IL50478A/xx unknown
- 1976-09-16 DE DE2641724A patent/DE2641724C2/de not_active Expired
- 1976-09-16 FR FR7627888A patent/FR2324636A1/fr active Granted
- 1976-09-17 NO NO763188A patent/NO763188L/no unknown
- 1976-09-17 CA CA261,472A patent/CA1062713A/en not_active Expired
- 1976-09-17 DD DD76203733A patent/DD135624A5/xx unknown
- 1976-09-17 DD DD7600194848A patent/DD129006A5/xx unknown
- 1976-09-17 JP JP51110953A patent/JPS5239685A/ja active Granted
- 1976-09-17 GB GB38596/76A patent/GB1510090A/en not_active Expired
- 1976-09-17 DK DK422376A patent/DK422376A/da not_active Application Discontinuation
- 1976-09-17 AT AT693276A patent/AT356111B/de not_active IP Right Cessation
- 1976-09-17 IT IT27349/76A patent/IT1068298B/it active
- 1976-09-20 SE SE7610422A patent/SE7610422L/xx unknown
-
1979
- 1979-01-11 HK HK21/79A patent/HK2179A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD135624A5 (de) | 1979-05-16 |
| AT356111B (de) | 1980-04-10 |
| FR2324636A1 (fr) | 1977-04-15 |
| JPS5239685A (en) | 1977-03-28 |
| SE7610422L (sv) | 1977-03-20 |
| US4062798A (en) | 1977-12-13 |
| IT1068298B (it) | 1985-03-21 |
| AU1771776A (en) | 1978-03-23 |
| NO763188L (no) | 1977-03-22 |
| HK2179A (en) | 1979-01-19 |
| ATA693276A (de) | 1979-09-15 |
| FR2324636B1 (enExample) | 1979-09-28 |
| IL50478A (en) | 1980-01-31 |
| IL50478A0 (en) | 1976-11-30 |
| JPS5527056B2 (enExample) | 1980-07-17 |
| DK422376A (da) | 1977-03-20 |
| GB1510090A (en) | 1978-05-10 |
| DE2641724A1 (de) | 1977-03-24 |
| DE2641724C2 (de) | 1982-07-01 |
| DD129006A5 (de) | 1977-12-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1062713A (en) | Pyrimidine derivatives | |
| DE2547737C2 (de) | Phenylpyrimidine | |
| EP0126949B1 (de) | Fluorhaltige Pyrimidinderivate | |
| US5055221A (en) | Smectic liquid-crystalline phases | |
| EP0104011B1 (en) | Pyrimidine derivatives | |
| US4180475A (en) | Liquid crystal mixtures | |
| KR970006720B1 (ko) | 액정 조성물 | |
| US4309539A (en) | Pyrimidine derivatives | |
| GB2042533A (en) | Cyclohexylpyrimidines useful in liquid crystalline mixtures and display devices | |
| JPS61501920A (ja) | 異方性化合物およびそれらを用いた液晶混合物 | |
| JPS6156137A (ja) | 液晶混合物 | |
| JPS63502284A (ja) | ビニレン化合物 | |
| JPS62501361A (ja) | ピリミジン化合物 | |
| GB2085877A (en) | Liquid crystal trans-(4-alkyl cyclohexyl) pyrimidines | |
| US5759443A (en) | Cyclopentyl derivatives | |
| EP0277815B1 (en) | Optically active-2-alkoxy-propyl ether and liquid crystal composition | |
| US4623477A (en) | Ester compounds having a pyrimidine ring | |
| US4066570A (en) | Phenyl-pyrimidines | |
| Villiger et al. | Synthesis and Mesomorphic Properties of New Liquid Crystalline Cyclohexyl-phenyl-and Dicyclohexyl-pyrimidines | |
| US4818430A (en) | 3,6-diphenylpyridazines | |
| CA1082706A (en) | Optically active compounds | |
| EP0186045A1 (en) | 1,4-Dipyrimidinylbenzene derivative and liquid crystal composition containing it | |
| Kelly et al. | 2-(4-Alkylphenyl)-5-(alkenyloxy) pyrimidines: Synthesis, liquid crystal transition temperatures and some physical properties | |
| JPS63301872A (ja) | スメクチック性液晶化合物 | |
| CH622548A5 (en) | Liquid-crystal mixtures |