AR060225A1 - Proceso para preparar 6,7- dihidro-5h-imidazo (1,5-a) piridin -8- ona - Google Patents
Proceso para preparar 6,7- dihidro-5h-imidazo (1,5-a) piridin -8- onaInfo
- Publication number
- AR060225A1 AR060225A1 ARP070101337A ARP070101337A AR060225A1 AR 060225 A1 AR060225 A1 AR 060225A1 AR P070101337 A ARP070101337 A AR P070101337A AR P070101337 A ARP070101337 A AR P070101337A AR 060225 A1 AR060225 A1 AR 060225A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- imidazo
- converted
- pyridin
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 abstract 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 4
- SPZRVKIZAPHPOR-UHFFFAOYSA-N 6,7-dihydro-5h-imidazo[1,5-a]pyridin-8-one Chemical compound O=C1CCCN2C=NC=C12 SPZRVKIZAPHPOR-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000003158 alcohol group Chemical group 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- SKVRYQUMKJQZFN-UHFFFAOYSA-N hydron;2-(hydroxymethyl)pyridin-3-ol;chloride Chemical compound Cl.OCC1=NC=CC=C1O SKVRYQUMKJQZFN-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000003328 mesylation reaction Methods 0.000 abstract 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 abstract 1
- 150000003138 primary alcohols Chemical class 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Reivindicacion 1: Un proceso para preparar 6,7-dihidro-5H-imidazo[1,5-a]piridin-8-ona (formula 1) caracterizado porque un compuesto de formula 8, donde R4 es un grupo protector adecuado que se puede eliminar por hidrogenacion en determinadas condiciones, por ejemplo bencilo o 4-metoxibencilo, se hidrogena selectivamente en la funcionalidad ciano para obtener un compuesto de formula 9 o el clorhidrato de 2-hidroximetilpiridin-3-ol (formula 8') se convierte, por O-alquilacion catalizada por transferencia de fase selectiva del alcohol en la posicion 3 con un R4-haluro, seguido por la mesilacion del alcohol primario, la reaccion con ftalimida de potasio y el posterior tratamiento con solucion acuosa de dimetilamina, preferentemente solucion acuosa de dimetilamina al 40%, en un compuesto de formula 9, 2b) el compuesto de formula 9 se convierte por reaccion con ácido formico para obtener el compuesto de formula 10, 2c) el compuesto de formula 10 se convierte en el compuesto de formula 11, y 2d) el compuesto de formula 11 se hidrogena para obtener 6,7-dihidro-5H-imidazo[1,5-a]piridin-8-ona (formula 1).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH5352006 | 2006-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR060225A1 true AR060225A1 (es) | 2008-06-04 |
Family
ID=38166492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP070101337A AR060225A1 (es) | 2006-03-31 | 2007-03-29 | Proceso para preparar 6,7- dihidro-5h-imidazo (1,5-a) piridin -8- ona |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20090118512A1 (es) |
| EP (1) | EP2001850A1 (es) |
| JP (1) | JP2009531391A (es) |
| CN (1) | CN101410377A (es) |
| AR (1) | AR060225A1 (es) |
| BR (1) | BRPI0709695A2 (es) |
| CA (1) | CA2647616A1 (es) |
| IL (1) | IL194384A0 (es) |
| TW (1) | TW200804284A (es) |
| WO (1) | WO2007113235A1 (es) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1329394C (zh) * | 2000-11-17 | 2007-08-01 | 武田药品工业株式会社 | 新咪唑衍生物、其制备方法及其用途 |
| TW200612947A (en) * | 2004-05-28 | 2006-05-01 | Speedel Experimenta Ag | Organic compounds |
| FR2883286B1 (fr) * | 2005-03-16 | 2008-10-03 | Sanofi Aventis Sa | NOUVEAUX DERIVES D'IMIDAZO[1,5-a]PYRIDINES, INHIBITEURS DE FGFs, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES LES CONTENANT |
-
2007
- 2007-03-29 AR ARP070101337A patent/AR060225A1/es unknown
- 2007-03-29 TW TW096110915A patent/TW200804284A/zh unknown
- 2007-03-30 JP JP2009502106A patent/JP2009531391A/ja active Pending
- 2007-03-30 CN CNA2007800113578A patent/CN101410377A/zh active Pending
- 2007-03-30 CA CA002647616A patent/CA2647616A1/en not_active Abandoned
- 2007-03-30 BR BRPI0709695-0A patent/BRPI0709695A2/pt not_active Application Discontinuation
- 2007-03-30 WO PCT/EP2007/053078 patent/WO2007113235A1/en active Application Filing
- 2007-03-30 US US12/225,813 patent/US20090118512A1/en not_active Abandoned
- 2007-03-30 EP EP07727550A patent/EP2001850A1/en not_active Withdrawn
-
2008
- 2008-09-25 IL IL194384A patent/IL194384A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN101410377A (zh) | 2009-04-15 |
| JP2009531391A (ja) | 2009-09-03 |
| IL194384A0 (en) | 2009-08-03 |
| WO2007113235A1 (en) | 2007-10-11 |
| CA2647616A1 (en) | 2007-10-11 |
| EP2001850A1 (en) | 2008-12-17 |
| TW200804284A (en) | 2008-01-16 |
| US20090118512A1 (en) | 2009-05-07 |
| BRPI0709695A2 (pt) | 2011-07-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |