SU458130A3 - Способ получени нитрофурилпириидиновых производных - Google Patents
Способ получени нитрофурилпириидиновых производныхInfo
- Publication number
- SU458130A3 SU458130A3 SU1754975A SU1754975A SU458130A3 SU 458130 A3 SU458130 A3 SU 458130A3 SU 1754975 A SU1754975 A SU 1754975A SU 1754975 A SU1754975 A SU 1754975A SU 458130 A3 SU458130 A3 SU 458130A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- furyl
- pyrimidine
- solution
- ethyl acetate
- yield
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 52
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000243 solution Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- 239000000047 product Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- -1 acetoxyethylamino Chemical group 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- AEXIQPQOFKQACC-UHFFFAOYSA-N 2-ethoxypyrimidine Chemical compound CCOC1=NC=CC=N1 AEXIQPQOFKQACC-UHFFFAOYSA-N 0.000 description 10
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229910017604 nitric acid Inorganic materials 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LAIZBXNIUKWPOC-UHFFFAOYSA-N 2-(furan-2-yl)-4-nitropyrimidine Chemical class [N+](=O)([O-])C1=NC(=NC=C1)C=1OC=CC1 LAIZBXNIUKWPOC-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MWBLQQNQHOTLGM-UHFFFAOYSA-N 2-[2-(furan-2-yl)pyrimidin-5-yl]oxy-N-methylethanamine Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCNC MWBLQQNQHOTLGM-UHFFFAOYSA-N 0.000 description 2
- XQQIGLPLFSRAJT-UHFFFAOYSA-N 2-[2-(furan-2-yl)pyrimidin-5-yl]oxyethyl 4-methylbenzenesulfonate Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCOS(=O)(=O)C1=CC=C(C=C1)C XQQIGLPLFSRAJT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- MZOQFVRUZANWKO-UHFFFAOYSA-N 2-ethoxypyrimidine hydrochloride Chemical compound Cl.CCOc1ncccn1 MZOQFVRUZANWKO-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000191291 Abies alba Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SWBPBKJXEPIRGN-UHFFFAOYSA-N Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNC Chemical compound Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNC SWBPBKJXEPIRGN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2113529A DE2113529C3 (de) | 1971-03-17 | 1971-03-17 | 2-(5-Nitro-2-furyl)-5-(2-alkylaminoäthoxy)-pyrimidin-Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU458130A3 true SU458130A3 (ru) | 1975-01-25 |
Family
ID=5802207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1754975A SU458130A3 (ru) | 1971-03-17 | 1972-03-02 | Способ получени нитрофурилпириидиновых производных |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3846428A (enExample) |
| AT (1) | AT312589B (enExample) |
| AU (1) | AU463550B2 (enExample) |
| BE (1) | BE780879A (enExample) |
| CA (1) | CA945557A (enExample) |
| CH (1) | CH575943A5 (enExample) |
| DD (1) | DD96950A5 (enExample) |
| DE (1) | DE2113529C3 (enExample) |
| DK (1) | DK126999B (enExample) |
| ES (1) | ES400560A1 (enExample) |
| FR (1) | FR2130327B1 (enExample) |
| GB (1) | GB1391933A (enExample) |
| HU (1) | HU163178B (enExample) |
| IL (1) | IL38962A (enExample) |
| NL (1) | NL7203650A (enExample) |
| PL (1) | PL83278B1 (enExample) |
| SU (1) | SU458130A3 (enExample) |
| ZA (1) | ZA721689B (enExample) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1937629C3 (de) * | 1969-07-19 | 1979-07-26 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Nitrofuryl-aminoalkoxy-pyriinidine |
-
1971
- 1971-03-17 DE DE2113529A patent/DE2113529C3/de not_active Expired
-
1972
- 1972-02-29 DK DK93172AA patent/DK126999B/da unknown
- 1972-03-02 SU SU1754975A patent/SU458130A3/ru active
- 1972-03-08 AU AU39769/72A patent/AU463550B2/en not_active Expired
- 1972-03-08 ES ES400560A patent/ES400560A1/es not_active Expired
- 1972-03-12 IL IL38962A patent/IL38962A/xx unknown
- 1972-03-13 GB GB1152872A patent/GB1391933A/en not_active Expired
- 1972-03-13 ZA ZA721689A patent/ZA721689B/xx unknown
- 1972-03-15 PL PL1972154083A patent/PL83278B1/pl unknown
- 1972-03-15 DD DD161547A patent/DD96950A5/xx unknown
- 1972-03-16 US US00235426A patent/US3846428A/en not_active Expired - Lifetime
- 1972-03-16 HU HUSC379A patent/HU163178B/hu unknown
- 1972-03-16 FR FR7209187A patent/FR2130327B1/fr not_active Expired
- 1972-03-16 CH CH385372A patent/CH575943A5/xx not_active IP Right Cessation
- 1972-03-17 BE BE780879A patent/BE780879A/xx unknown
- 1972-03-17 CA CA137,369A patent/CA945557A/en not_active Expired
- 1972-03-17 NL NL7203650A patent/NL7203650A/xx unknown
- 1972-03-17 AT AT230072A patent/AT312589B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL38962A (en) | 1975-10-15 |
| GB1391933A (en) | 1975-04-23 |
| ES400560A1 (es) | 1975-02-01 |
| AU3976972A (en) | 1973-09-13 |
| CH575943A5 (enExample) | 1976-05-31 |
| DE2113529A1 (de) | 1972-12-14 |
| US3846428A (en) | 1974-11-05 |
| BE780879A (fr) | 1972-09-18 |
| PL83278B1 (enExample) | 1975-12-31 |
| HU163178B (enExample) | 1973-06-28 |
| FR2130327B1 (enExample) | 1975-04-25 |
| IL38962A0 (en) | 1972-05-30 |
| DE2113529C3 (de) | 1980-04-30 |
| NL7203650A (enExample) | 1972-09-19 |
| FR2130327A1 (enExample) | 1972-11-03 |
| CA945557A (en) | 1974-04-16 |
| AT312589B (de) | 1974-01-10 |
| AU463550B2 (en) | 1975-07-14 |
| DK126999B (da) | 1973-09-10 |
| ZA721689B (en) | 1972-12-27 |
| DD96950A5 (enExample) | 1973-04-12 |
| DE2113529B2 (de) | 1979-08-02 |
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