CH511873A - Procédé de préparation d'imidazopyridines - Google Patents
Procédé de préparation d'imidazopyridinesInfo
- Publication number
- CH511873A CH511873A CH1737469A CH1737469A CH511873A CH 511873 A CH511873 A CH 511873A CH 1737469 A CH1737469 A CH 1737469A CH 1737469 A CH1737469 A CH 1737469A CH 511873 A CH511873 A CH 511873A
- Authority
- CH
- Switzerland
- Prior art keywords
- substituted
- anhydride
- acid
- alkyl
- reaction
- Prior art date
Links
- 150000005232 imidazopyridines Chemical class 0.000 title claims abstract description 11
- 239000004009 herbicide Substances 0.000 title abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 16
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- -1 amino, thio Chemical group 0.000 claims abstract description 11
- 238000010992 reflux Methods 0.000 claims abstract description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
- 150000001408 amides Chemical class 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 5
- SOWBFZRMHSNYGE-UHFFFAOYSA-N Monoamide-Oxalic acid Natural products NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- CRMACCRNCSJWTO-UHFFFAOYSA-N 2h-pyridine-1,2-diamine Chemical compound NC1C=CC=CN1N CRMACCRNCSJWTO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002577 pseudohalo group Chemical group 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- ZRCMCGQDIYNWDX-UHFFFAOYSA-N 5-chloropyridine-2,3-diamine Chemical compound NC1=CC(Cl)=CN=C1N ZRCMCGQDIYNWDX-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000004803 chlorobenzyl group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- GPBZAKVUCIOOFH-UHFFFAOYSA-N 6-chloro-2-ethyl-1h-imidazo[4,5-b]pyridine Chemical compound C1=C(Cl)C=C2NC(CC)=NC2=N1 GPBZAKVUCIOOFH-UHFFFAOYSA-N 0.000 description 1
- HAXLILLUFUXGBU-UHFFFAOYSA-N 6-chloro-2-propan-2-yl-1h-imidazo[4,5-b]pyridine Chemical compound C1=C(Cl)C=C2NC(C(C)C)=NC2=N1 HAXLILLUFUXGBU-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5542268 | 1968-11-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH511873A true CH511873A (fr) | 1971-08-31 |
Family
ID=10473858
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1737469A CH511873A (fr) | 1968-11-22 | 1969-11-21 | Procédé de préparation d'imidazopyridines |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH511873A (enrdf_load_stackoverflow) |
| ES (1) | ES373778A1 (enrdf_load_stackoverflow) |
| NL (1) | NL6917115A (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994022859A1 (de) * | 1993-03-26 | 1994-10-13 | Bayer Aktiengesellschaft | Substituierte, heteroanellierte imidazole und ihre verwendung als herbizide |
| US6448281B1 (en) | 2000-07-06 | 2002-09-10 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
| US7576079B2 (en) | 2001-07-25 | 2009-08-18 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
| US7582770B2 (en) | 2004-02-20 | 2009-09-01 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| US7838537B2 (en) | 2003-01-22 | 2010-11-23 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| US7888363B2 (en) | 2003-01-22 | 2011-02-15 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| US8076365B2 (en) | 2005-08-12 | 2011-12-13 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
-
1969
- 1969-11-13 NL NL6917115A patent/NL6917115A/xx unknown
- 1969-11-21 CH CH1737469A patent/CH511873A/fr not_active IP Right Cessation
- 1969-11-21 ES ES373778A patent/ES373778A1/es not_active Expired
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994022859A1 (de) * | 1993-03-26 | 1994-10-13 | Bayer Aktiengesellschaft | Substituierte, heteroanellierte imidazole und ihre verwendung als herbizide |
| US6448281B1 (en) | 2000-07-06 | 2002-09-10 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
| US6479508B1 (en) | 2000-07-06 | 2002-11-12 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
| US6794404B2 (en) | 2000-07-06 | 2004-09-21 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
| US7439258B2 (en) | 2000-07-06 | 2008-10-21 | Boehringer Ingelheim (Canada) Ltd | Viral polymerase inhibitors |
| US7576079B2 (en) | 2001-07-25 | 2009-08-18 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
| US7803944B2 (en) | 2001-07-25 | 2010-09-28 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| US7893084B2 (en) | 2001-07-25 | 2011-02-22 | Boehringer Ingelheim Canada Ltd. | Viral polymerase inhibitors |
| US7888363B2 (en) | 2003-01-22 | 2011-02-15 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| US7838537B2 (en) | 2003-01-22 | 2010-11-23 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| US7582770B2 (en) | 2004-02-20 | 2009-09-01 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| US7879851B2 (en) | 2004-02-20 | 2011-02-01 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| US8030309B2 (en) | 2004-02-20 | 2011-10-04 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| US8076365B2 (en) | 2005-08-12 | 2011-12-13 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| ES373778A1 (es) | 1972-04-01 |
| NL6917115A (enrdf_load_stackoverflow) | 1970-05-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |