DE2302397A1 - Aminopyrazine und verfahren zu ihrer herstellung - Google Patents
Aminopyrazine und verfahren zu ihrer herstellungInfo
- Publication number
- DE2302397A1 DE2302397A1 DE2302397A DE2302397A DE2302397A1 DE 2302397 A1 DE2302397 A1 DE 2302397A1 DE 2302397 A DE2302397 A DE 2302397A DE 2302397 A DE2302397 A DE 2302397A DE 2302397 A1 DE2302397 A1 DE 2302397A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- aza
- reaction
- amino
- formula
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 28
- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 8
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 9
- 230000001476 alcoholic effect Effects 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- -1 cyano, carboxy Chemical group 0.000 claims description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000005891 transamination reaction Methods 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- TUVFMMNANXKTRP-UHFFFAOYSA-N Ethenamine, N-methylene- Chemical class C=CN=C TUVFMMNANXKTRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
- 150000001925 cycloalkenes Chemical class 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- GYSIANSTMOFIII-UHFFFAOYSA-N 2-(methylideneamino)ethenamine Chemical class NC=CN=C GYSIANSTMOFIII-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- LCUSJKHFDGIFGP-UHFFFAOYSA-N n'-ethenylmethanimidamide Chemical class NC=NC=C LCUSJKHFDGIFGP-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- 150000002923 oximes Chemical class 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 11
- 239000000155 melt Substances 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000003216 pyrazines Chemical class 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- UTCCARLHJKAWIA-ONEGZZNKSA-N 4-[(e)-but-1-enyl]morpholine Chemical compound CC\C=C\N1CCOCC1 UTCCARLHJKAWIA-ONEGZZNKSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- UTCCARLHJKAWIA-UHFFFAOYSA-N 4-but-1-enylmorpholine Chemical compound CCC=CN1CCOCC1 UTCCARLHJKAWIA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 125000005521 carbonamide group Chemical group 0.000 description 2
- 125000004989 dicarbonyl group Chemical group 0.000 description 2
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- PABFBVIKZYEEME-VMPITWQZSA-N 1-[(e)-pent-1-enyl]piperidine Chemical compound CCC\C=C\N1CCCCC1 PABFBVIKZYEEME-VMPITWQZSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- GPIZLEHIVRHDAW-UHFFFAOYSA-N 3-aminopyrazine-2-carbonitrile Chemical class NC1=NC=CN=C1C#N GPIZLEHIVRHDAW-UHFFFAOYSA-N 0.000 description 1
- IIQFBBQJYPGOHJ-UHFFFAOYSA-N 4-(cyclohexen-1-yl)morpholine Chemical compound C1CCCC(N2CCOCC2)=C1 IIQFBBQJYPGOHJ-UHFFFAOYSA-N 0.000 description 1
- VAPOFMGACKUWCI-UHFFFAOYSA-N 4-(cyclopenten-1-yl)morpholine Chemical compound C1CCC=C1N1CCOCC1 VAPOFMGACKUWCI-UHFFFAOYSA-N 0.000 description 1
- DICAOXCQWRAOQB-UHFFFAOYSA-N C=NC=CC1=CC=CC=C1 Chemical compound C=NC=CC1=CC=CC=C1 DICAOXCQWRAOQB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000002897 diene group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- FPRWQPODBBHISI-UHFFFAOYSA-N ethyl 2-cyano-2-(1-piperidin-1-ylpent-1-en-2-ylimino)acetate Chemical compound CCOC(=O)C(C#N)=NC(CCC)=CN1CCCCC1 FPRWQPODBBHISI-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- GWSYTJJRDBPAKI-UHFFFAOYSA-N methyl 3-amino-5-phenylpyrazine-2-carboxylate Chemical compound N1=C(N)C(C(=O)OC)=NC=C1C1=CC=CC=C1 GWSYTJJRDBPAKI-UHFFFAOYSA-N 0.000 description 1
- PIDIDDGZABWDLP-UHFFFAOYSA-N methyl 3-amino-6-methyl-5-phenylpyrazine-2-carboxylate Chemical compound N1=C(N)C(C(=O)OC)=NC(C)=C1C1=CC=CC=C1 PIDIDDGZABWDLP-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003195 pteridines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7201854A FR2168683A5 (enExample) | 1972-01-20 | 1972-01-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2302397A1 true DE2302397A1 (de) | 1973-07-26 |
Family
ID=9092178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2302397A Pending DE2302397A1 (de) | 1972-01-20 | 1973-01-18 | Aminopyrazine und verfahren zu ihrer herstellung |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3932404A (enExample) |
| JP (1) | JPS4880578A (enExample) |
| BE (1) | BE794329A (enExample) |
| CH (1) | CH561187A5 (enExample) |
| DE (1) | DE2302397A1 (enExample) |
| FR (1) | FR2168683A5 (enExample) |
| GB (1) | GB1393332A (enExample) |
| IT (1) | IT1036046B (enExample) |
| NL (1) | NL7300652A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0018144A1 (en) * | 1979-04-06 | 1980-10-29 | Eli Lilly And Company | A process for the preparation of substituted 2-aminopyrazines |
-
0
- BE BE794329D patent/BE794329A/xx unknown
-
1972
- 1972-01-20 FR FR7201854A patent/FR2168683A5/fr not_active Expired
- 1972-12-29 IT IT71247/72A patent/IT1036046B/it active
-
1973
- 1973-01-17 NL NL7300652A patent/NL7300652A/xx not_active Application Discontinuation
- 1973-01-17 CH CH63873A patent/CH561187A5/xx not_active IP Right Cessation
- 1973-01-18 DE DE2302397A patent/DE2302397A1/de active Pending
- 1973-01-19 JP JP48008459A patent/JPS4880578A/ja active Pending
- 1973-01-22 GB GB311173A patent/GB1393332A/en not_active Expired
- 1973-03-21 US US05/343,590 patent/US3932404A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0018144A1 (en) * | 1979-04-06 | 1980-10-29 | Eli Lilly And Company | A process for the preparation of substituted 2-aminopyrazines |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1393332A (en) | 1975-05-07 |
| US3932404A (en) | 1976-01-13 |
| JPS4880578A (enExample) | 1973-10-29 |
| IT1036046B (it) | 1979-10-30 |
| FR2168683A5 (enExample) | 1973-08-31 |
| CH561187A5 (enExample) | 1975-04-30 |
| NL7300652A (enExample) | 1973-07-24 |
| BE794329A (fr) | 1973-07-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |