MX2012003023A - Sintesis del ester terc-butilico del acido (4-fluoro-3-piperidin-4 -il-bencil)-carbamico y sus productos intermedios. - Google Patents
Sintesis del ester terc-butilico del acido (4-fluoro-3-piperidin-4 -il-bencil)-carbamico y sus productos intermedios.Info
- Publication number
- MX2012003023A MX2012003023A MX2012003023A MX2012003023A MX2012003023A MX 2012003023 A MX2012003023 A MX 2012003023A MX 2012003023 A MX2012003023 A MX 2012003023A MX 2012003023 A MX2012003023 A MX 2012003023A MX 2012003023 A MX2012003023 A MX 2012003023A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- fluoro
- benzyl
- butyl ester
- carbamic acid
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 3
- 239000000543 intermediate Substances 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- MFRZZHOXGKQYOU-UHFFFAOYSA-N tert-butyl n-[(4-fluoro-3-piperidin-4-ylphenyl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=C(F)C(C2CCNCC2)=C1 MFRZZHOXGKQYOU-UHFFFAOYSA-N 0.000 title 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- PGFSQYFQVWFCSK-UHFFFAOYSA-N [2-fluoro-5-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]phenyl]boronic acid Chemical compound CC(C)(C)OC(=O)NCC1=CC=C(F)C(B(O)O)=C1 PGFSQYFQVWFCSK-UHFFFAOYSA-N 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- XMFJCIIONJPGFS-UHFFFAOYSA-N tert-butyl n-[(4-fluoro-2-pyridin-4-ylphenyl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=C(F)C=C1C1=CC=NC=C1 XMFJCIIONJPGFS-UHFFFAOYSA-N 0.000 abstract 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 abstract 1
- -1 4-fluoro-3-piperidin-4-yl-benzyl Chemical group 0.000 abstract 1
- 238000006069 Suzuki reaction reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- 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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
La presente invención consiste en un método mejorado para la preparación del éster terc-butílico del ácido (4-fluoro-3-piperidin-4-il-bencil)-carbámico, compuesto of fórmula I. La invención está dirigida a un método de síntesis para el compuesto of fórmula I en tres etapas, que comprende la formación de ácido 5-((terc-butoxicarbonil)aminometil)-2-fluoroben ceno-borónico (compuesto 11), la reacción del compuesto 11 en condiciones de acoplamiento de Suzuki para proporcionar el éster terc-butílico del ácido (4-fluoro-2-piridin-4-il-bencil)-carbámico y la hidrogenación selectiva del producto antes mencionado en condiciones de hidrogenación que proporciona el compuesto I. La invención se refiere también a los compuestos intermedios ácido 5-((terc-butoxicarbonil)amino-metil)-2-fluorobenceno-borónico (compuesto 11) y éster terc-butílico del ácido (4-fiuoro-2-pindin-4-iI-bencil)-carbámico (compuesto 13).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24532509P | 2009-09-24 | 2009-09-24 | |
| PCT/US2010/049737 WO2011037947A1 (en) | 2009-09-24 | 2010-09-22 | Synthesis of (4-fluoro-3-piperidin-4-yl-benzyl)-carbamic acid tert-butyl ester and intermediates thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2012003023A true MX2012003023A (es) | 2012-04-10 |
Family
ID=42984934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2012003023A MX2012003023A (es) | 2009-09-24 | 2010-09-22 | Sintesis del ester terc-butilico del acido (4-fluoro-3-piperidin-4 -il-bencil)-carbamico y sus productos intermedios. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8633321B2 (es) |
| EP (1) | EP2483243B1 (es) |
| JP (1) | JP2013505935A (es) |
| KR (1) | KR20120083357A (es) |
| CN (1) | CN102574792B (es) |
| AU (1) | AU2010298425A1 (es) |
| BR (1) | BR112012006519A2 (es) |
| CA (1) | CA2774614C (es) |
| IL (1) | IL218680A0 (es) |
| MX (1) | MX2012003023A (es) |
| MY (1) | MY155682A (es) |
| RU (1) | RU2543483C2 (es) |
| SG (1) | SG179201A1 (es) |
| WO (1) | WO2011037947A1 (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2012003023A (es) | 2009-09-24 | 2012-04-10 | Sanofi Aventis Us Llc | Sintesis del ester terc-butilico del acido (4-fluoro-3-piperidin-4 -il-bencil)-carbamico y sus productos intermedios. |
| JP5859010B2 (ja) * | 2010-09-27 | 2016-02-10 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | ２−アミノ−ｎ−（２，２，２−トリフルオロエチル）アセトアミドの調製方法 |
| JP6578116B2 (ja) * | 2015-03-25 | 2019-09-18 | 公益財団法人相模中央化学研究所 | 一置換（フルオロアルキル）エチレン類及びその製造方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8912339D0 (en) * | 1989-05-30 | 1989-07-12 | Merck Patent Gmbh | Fluorinated biphenyl derivatives |
| US6248103B1 (en) | 1994-04-05 | 2001-06-19 | The Regents Of The University Of California | Apparatus and method for dynamic cooling of biological tissues for thermal mediated surgery using long laser pulses |
| DE10101022A1 (de) * | 2001-01-11 | 2002-07-18 | Clariant Internat Ltd Muttenz | Fluorierte Aromaten und ihre Verwendung in Flüssigkristallmischungen |
| JP2005111003A (ja) * | 2003-10-08 | 2005-04-28 | Kita Denshi Corp | 遊技場システム、現金管理装置及び搬送異常検出方法 |
| EP1571150A1 (en) * | 2004-03-02 | 2005-09-07 | Aventis Pharma Deutschland GmbH | Process for the preparation of tryptase inhibitors |
| DOP2005000039A (es) * | 2004-03-26 | 2005-10-31 | Aventis Pharma Inc | Hidrocloruro de [4-(5-aminometil-2-fluoro-fenil)- piperidin-1-il]-(4-bomo-3-metil-5-propoxi-tiofen-2-il)-metanona como un inhibidor de la triptasa de mastocitos |
| MXPA06012595A (es) * | 2004-04-29 | 2007-05-09 | Abbott Lab | Analogos de amino-tetrazoles y metodos de uso. |
| MX2012003023A (es) | 2009-09-24 | 2012-04-10 | Sanofi Aventis Us Llc | Sintesis del ester terc-butilico del acido (4-fluoro-3-piperidin-4 -il-bencil)-carbamico y sus productos intermedios. |
-
2010
- 2010-09-22 MX MX2012003023A patent/MX2012003023A/es active IP Right Grant
- 2010-09-22 CA CA2774614A patent/CA2774614C/en not_active Expired - Fee Related
- 2010-09-22 CN CN201080042702.6A patent/CN102574792B/zh active Active
- 2010-09-22 KR KR1020127007644A patent/KR20120083357A/ko not_active Application Discontinuation
- 2010-09-22 BR BR112012006519A patent/BR112012006519A2/pt not_active IP Right Cessation
- 2010-09-22 RU RU2012116346/04A patent/RU2543483C2/ru not_active IP Right Cessation
- 2010-09-22 MY MYPI2012001233A patent/MY155682A/en unknown
- 2010-09-22 EP EP10757923.7A patent/EP2483243B1/en active Active
- 2010-09-22 JP JP2012530984A patent/JP2013505935A/ja not_active Ceased
- 2010-09-22 WO PCT/US2010/049737 patent/WO2011037947A1/en active Application Filing
- 2010-09-22 SG SG2012018958A patent/SG179201A1/en unknown
- 2010-09-22 AU AU2010298425A patent/AU2010298425A1/en not_active Abandoned
-
2012
- 2012-03-15 IL IL218680A patent/IL218680A0/en unknown
- 2012-03-22 US US13/426,721 patent/US8633321B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| RU2543483C2 (ru) | 2015-03-10 |
| AU2010298425A1 (en) | 2012-04-19 |
| CN102574792B (zh) | 2014-07-09 |
| IL218680A0 (en) | 2012-05-31 |
| EP2483243B1 (en) | 2015-03-18 |
| RU2012116346A (ru) | 2013-10-27 |
| MY155682A (en) | 2015-11-13 |
| CN102574792A (zh) | 2012-07-11 |
| US8633321B2 (en) | 2014-01-21 |
| JP2013505935A (ja) | 2013-02-21 |
| CA2774614C (en) | 2015-03-10 |
| EP2483243A1 (en) | 2012-08-08 |
| CA2774614A1 (en) | 2011-03-31 |
| KR20120083357A (ko) | 2012-07-25 |
| US20120184745A1 (en) | 2012-07-19 |
| BR112012006519A2 (pt) | 2015-09-08 |
| SG179201A1 (en) | 2012-05-30 |
| WO2011037947A1 (en) | 2011-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant or registration |