WO2005099712A3 - Process for preparation of n-[3-(3-cyanopyrazolo [1,5-a]pyrimidin-7-yl)phenyl]-n-ethylacetamide - Google Patents

Process for preparation of n-[3-(3-cyanopyrazolo [1,5-a]pyrimidin-7-yl)phenyl]-n-ethylacetamide Download PDF

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Publication number
WO2005099712A3
WO2005099712A3 PCT/IN2005/000119 IN2005000119W WO2005099712A3 WO 2005099712 A3 WO2005099712 A3 WO 2005099712A3 IN 2005000119 W IN2005000119 W IN 2005000119W WO 2005099712 A3 WO2005099712 A3 WO 2005099712A3
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WO
WIPO (PCT)
Prior art keywords
ethylacetamide
phenyl
cyanopyrazolo
pyrimidin
water
Prior art date
Application number
PCT/IN2005/000119
Other languages
French (fr)
Other versions
WO2005099712A2 (en
Inventor
Rajaram Sankara Subramanian
Natarajan Sathyanarayanan
Prasad Nagaraja Rao Janardhana
Balasubramaniam Sivaraman
Munusamy Jayamani
R Bapat Uday
Original Assignee
Sanmar Speciality Chemicals Lt
Rajaram Sankara Subramanian
Natarajan Sathyanarayanan
Prasad Nagaraja Rao Janardhana
Balasubramaniam Sivaraman
Munusamy Jayamani
R Bapat Uday
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.)
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Publication date
Application filed by Sanmar Speciality Chemicals Lt, Rajaram Sankara Subramanian, Natarajan Sathyanarayanan, Prasad Nagaraja Rao Janardhana, Balasubramaniam Sivaraman, Munusamy Jayamani, R Bapat Uday filed Critical Sanmar Speciality Chemicals Lt
Publication of WO2005099712A2 publication Critical patent/WO2005099712A2/en
Publication of WO2005099712A3 publication Critical patent/WO2005099712A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

An improved process for preparing N-[3-(3-Cyanopyrazolo [1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamide, (zaleplon), comprising the steps of reacting N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-ethylacetamide with 3-amino-4-cyanopyrazole in a reaction medium comprising (i) water and water-immiscible organic solvents in presence of either organic sulphonic acids or Lewis acids; (ii) aromatic hydrocarbons as solvent in presence of either organic sulphonic acids or Lewis acids; or (iii) water and organic sulphonic acid or Lewis acids.
PCT/IN2005/000119 2004-04-19 2005-04-19 Process for preparation of n-[3-(3-cyanopyrazolo [1,5-a]pyrimidin-7-yl)phenyl]-n-ethylacetamide WO2005099712A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN359/CHE/2004 2004-04-19
IN359CH2004 2004-04-19

Publications (2)

Publication Number Publication Date
WO2005099712A2 WO2005099712A2 (en) 2005-10-27
WO2005099712A3 true WO2005099712A3 (en) 2006-12-21

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PCT/IN2005/000119 WO2005099712A2 (en) 2004-04-19 2005-04-19 Process for preparation of n-[3-(3-cyanopyrazolo [1,5-a]pyrimidin-7-yl)phenyl]-n-ethylacetamide

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WO (1) WO2005099712A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102584831A (en) * 2011-12-29 2012-07-18 蚌埠丰原涂山制药有限公司 Preparation method for zaleplon
CN105622615A (en) * 2015-12-30 2016-06-01 上海天慈国际药业有限公司 Novel method for synthesizing zaleplon

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030040522A1 (en) * 2001-06-12 2003-02-27 Ferenc Korodi Process for the production of N-[3-(3-cyanopyrazolo[1,5-a] pyrimidin-7-yl) phenyl]-N-ethylacetamide (zaleplon)
WO2005070931A1 (en) * 2004-01-14 2005-08-04 Mallinckrodt Inc. Two-phase method for the synthesis of selected pyrazolopyrimidines
WO2005073235A2 (en) * 2004-02-02 2005-08-11 Richter Gedeon Vegyészeti Gyár Rt. Process for the synthesis of n- [3-(3-cyanopyrazolo [1,5a] pyrimidin-7-yl)-phenyl]-n-ethyl-acetamide

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030040522A1 (en) * 2001-06-12 2003-02-27 Ferenc Korodi Process for the production of N-[3-(3-cyanopyrazolo[1,5-a] pyrimidin-7-yl) phenyl]-N-ethylacetamide (zaleplon)
WO2005070931A1 (en) * 2004-01-14 2005-08-04 Mallinckrodt Inc. Two-phase method for the synthesis of selected pyrazolopyrimidines
WO2005073235A2 (en) * 2004-02-02 2005-08-11 Richter Gedeon Vegyészeti Gyár Rt. Process for the synthesis of n- [3-(3-cyanopyrazolo [1,5a] pyrimidin-7-yl)-phenyl]-n-ethyl-acetamide

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ALMANSA ET AL.: "Synthesis and SAR of a New Series of COX-2-Selective Inhibitors: Pyrazolo[1,5-a]pyrimidines", J. MED. CHEM., vol. 44, 2001, pages 350 - 361, XP002308586 *

Also Published As

Publication number Publication date
WO2005099712A2 (en) 2005-10-27

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