AR110356A1 - PROCESS FOR THE PREPARATION OF 2- (3- (FLUORMET) AZETIDIN-1-IL) ETAN-1-OL - Google Patents

PROCESS FOR THE PREPARATION OF 2- (3- (FLUORMET) AZETIDIN-1-IL) ETAN-1-OL

Info

Publication number
AR110356A1
AR110356A1 ARP170103481A ARP170103481A AR110356A1 AR 110356 A1 AR110356 A1 AR 110356A1 AR P170103481 A ARP170103481 A AR P170103481A AR P170103481 A ARP170103481 A AR P170103481A AR 110356 A1 AR110356 A1 AR 110356A1
Authority
AR
Argentina
Prior art keywords
formula
azetidin
fluoromethyl
tetrahydro
oxy
Prior art date
Application number
ARP170103481A
Other languages
Spanish (es)
Original Assignee
Hoffmann La Roche
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of AR110356A1 publication Critical patent/AR110356A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)

Abstract

Se describen métodos de preparación de 2-(3-(fluormetil)azetidin-1-il)etan-1-ol de fórmula (1), un producto intermedio útil para la síntesis de compuestos modulares del receptor de estrógeno. Reivindicación 1: Un proceso para la preparación de 2-(3-(fluormetil)azetidin-1-il)etan-1-ol de fórmula (1) que comprende hacer reaccionar 3-(fluormetil)azetidina de fórmula (2), glioxalato de etilo, y un primer agente reductor de hidruro para formar 2-(3-(fluormetil)azetidin-1-il)acetato de etilo de fórmula (3); y hacer reaccionar el compuesto de fórmula (3) con un segundo agente reductor de hidruro para formar el compuesto de fórmula (1). Reivindicación 17: El proceso de la reivindicación 1, que además comprende hacer reaccionar el compuesto de fórmula (1) y 2-(4-yodofenil)-4-metil-6-((tetrahidro-2H-piran-2-il)oxi)-3-(3-((tetrahidro-2H-piran-2-il)oxi)-2H-cromeno de fórmula (4) para formar 3-(fluormetil)-1-(2-(4-(4-metil-6-((tetrahidro-2H-piran-2-il)oxi)-3-(3-((tetrahidro-2H-piran-2-il)oxi)fenil)-2H-cromen-2-il)fenoxi)etil)azetidina de fórmula (5). Reivindicación 18: El proceso de la reivindicación 17, que además comprende hacer reaccionar el compuesto de fórmula (5) con ácido acético acuoso para formar 2-(4-(2-(3-(fluormetil)azetidin-1-ii)etoxi)fenil)-3-(3-hidroxifenil)-4-metil-2H-cromen-6-ol de fórmula (6).Methods of preparing 2- (3- (fluoromethyl) azetidin-1-yl) ethan-1-ol of formula (1), an intermediate useful for the synthesis of estrogen receptor modular compounds, are described. Claim 1: A process for the preparation of 2- (3- (fluormethyl) azetidin-1-yl) ethan-1-ol of formula (1) comprising reacting 3- (fluormethyl) azetidine of formula (2), glyoxalate ethyl, and a first hydride reducing agent to form ethyl 2- (3- (fluoromethyl) azetidin-1-yl) acetate of formula (3); and reacting the compound of formula (3) with a second hydride reducing agent to form the compound of formula (1). Claim 17: The process of claim 1, further comprising reacting the compound of formula (1) and 2- (4-iodophenyl) -4-methyl-6 - ((tetrahydro-2H-pyran-2-yl) oxy ) -3- (3 - ((tetrahydro-2H-pyran-2-yl) oxy) -2H-chromene of formula (4) to form 3- (fluoromethyl) -1- (2- (4- (4-methyl -6 - ((tetrahydro-2H-piran-2-yl) oxy) -3- (3 - ((tetrahydro-2H-piran-2-yl) oxy) phenyl) -2H-chromen-2-yl) phenoxy) ethyl) azetidine of formula (5) Claim 18: The process of claim 17, further comprising reacting the compound of formula (5) with aqueous acetic acid to form 2- (4- (2- (3- (fluoromethyl) ) azetidin-1-ii) ethoxy) phenyl) -3- (3-hydroxyphenyl) -4-methyl-2H-chromen-6-ol of formula (6).

ARP170103481A 2016-12-12 2017-12-13 PROCESS FOR THE PREPARATION OF 2- (3- (FLUORMET) AZETIDIN-1-IL) ETAN-1-OL AR110356A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US201662432837P 2016-12-12 2016-12-12

Publications (1)

Publication Number Publication Date
AR110356A1 true AR110356A1 (en) 2019-03-20

Family

ID=60935792

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP170103481A AR110356A1 (en) 2016-12-12 2017-12-13 PROCESS FOR THE PREPARATION OF 2- (3- (FLUORMET) AZETIDIN-1-IL) ETAN-1-OL

Country Status (2)

Country Link
AR (1) AR110356A1 (en)
WO (1) WO2018108954A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI702219B (en) 2018-07-12 2020-08-21 美商美國禮來大藥廠 Selective estrogen receptor degraders
CN114933551B (en) * 2022-06-28 2023-06-30 吉尔多肽生物制药(大连市)有限公司 Synthesis method of chiral Fmoc-3-amino-2- (tert-butoxymethyl) propionic acid

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008514595A (en) * 2004-09-24 2008-05-08 アストラゼネカ・アクチエボラーグ Compound, composition containing it, its production and its use II
NZ566793A (en) * 2005-08-24 2010-03-26 Eisai R&D Man Co Ltd Novel pyridine derivative and pyrimidine derivative
EA029559B1 (en) 2011-12-14 2018-04-30 Серагон Фармасьютикалс, Инк. Fluorinated estrogen receptor modulators and use thereof
AU2014281511A1 (en) 2013-06-19 2015-12-03 Seragon Pharmaceuticals, Inc. Estrogen receptor modulator and uses thereof
RU2015152171A (en) 2013-06-19 2017-07-25 Серагон Фармасьютикалз, Инк. ASETIDINE MODULATORS OF ESTROGEN RECEPTORS AND THEIR APPLICATION
KR102559719B1 (en) 2014-12-18 2023-07-26 에프. 호프만-라 로슈 아게 TETRAHYDRO-PYRIDO[3,4-b]INDOLE ESTROGEN RECEPTOR MODULATORS AND USES THEREOF
WO2016097071A1 (en) 2014-12-18 2016-06-23 F. Hoffmann-La Roche Ag Estrogen receptor modulators and uses thereof
EP3233818A1 (en) 2014-12-18 2017-10-25 F. Hoffmann-La Roche AG Derivatives of 2,3-diphenylchromene useful for the treatment of cancer

Also Published As

Publication number Publication date
WO2018108954A1 (en) 2018-06-21

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