JP2007531748A - ピロール−2−カルボニトリルの合成 - Google Patents
ピロール−2−カルボニトリルの合成 Download PDFInfo
- Publication number
- JP2007531748A JP2007531748A JP2007506458A JP2007506458A JP2007531748A JP 2007531748 A JP2007531748 A JP 2007531748A JP 2007506458 A JP2007506458 A JP 2007506458A JP 2007506458 A JP2007506458 A JP 2007506458A JP 2007531748 A JP2007531748 A JP 2007531748A
- Authority
- JP
- Japan
- Prior art keywords
- pyrrole
- carbonitrile
- solution phase
- solvent
- dialkylformamide
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
Claims (18)
- ピロール−2−カルボニトリルの調製法であって:
(a)ピロールを溶媒の存在下でクロロスルホニルイソシアネートと反応させ;
(b)工程(a)の生成物をモル過剰量のN,N−ジアルキルホルムアミドと接触させ;
(c)工程(b)の生成物をモル過剰量の有機塩基と接触させ、その結果、沈殿および溶液相が生成し;
(d)溶液相から沈殿を分離し;
(e)工程(d)の溶液相からピロール−2−カルボニトリルを単離することを含む方法。 - 少なくとも約2.0モル当量のN,N−ジアルキルホルムアミドが工程(b)において使用される請求項1記載の方法。
- 前記有機塩基が、ターシャリーアミンまたは芳香族アミンである請求項1記載の方法。
- 少なくとも約2.0モル当量のターシャリーアミンまたは芳香族アミンが工程(c)において使用される請求項3記載の方法。
- ピロール−2−カルボニトリルが蒸留により単離される請求項1〜4のいずれか1つに記載の方法。
- ピロールが1−メチルピロールである請求項1〜5のいずれか1つに記載の方法。
- 溶媒がトルエンまたはアセトニトリルである請求項1〜6のいずれか1つに記載の方法。
- 溶媒がトルエンである請求項1〜6のいずれか1つに記載の方法。
- ターシャリーアミンがトリエチルアミンである請求項3〜8のいずれか1つに記載の方法。
- 芳香族アミンがピリジンである請求項3〜8のいずれか1つに記載の方法。
- N,N−ジアルキルホルムアミドがN,N−ジメチルホルムアミド、N−ホルミルピペリジンまたはN−ホルミルモルホリンである請求項1〜10のいずれか1つに記載の方法。
- N,N−ジアルキルホルムアミドがN,N−ジメチルホルムアミドである請求項1〜10のいずれか1つに記載の方法。
- ピロールとクロロスルホニルイソシアネートのモル比が0.9:1〜1.1:1である請求項1〜12のいずれか1つに記載の方法。
- ピロール−2−カルボニトリルを工程(d)の溶液相から蒸留する前に、溶液相に水が添加される請求項5記載の方法。
- 溶媒1当量当たり0.1〜0.4モル当量の水が使用される請求項14記載の方法。
- 工程(d)の溶液相が、工程(e)における水の添加の前に濃縮される請求項15記載の方法。
- 工程(a)が約0℃以下の温度で行われる請求項1〜16のいずれか1つに記載の方法。
- 請求項1〜17のいずれか1つに記載の方法により製造される生成物。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US55780704P | 2004-03-30 | 2004-03-30 | |
US60/557,807 | 2004-03-30 | ||
US11/086,061 US7399870B2 (en) | 2004-03-30 | 2005-03-22 | Synthesis of pyrrole-2-carbonitriles |
US11/086,061 | 2005-03-22 | ||
PCT/US2005/010468 WO2005097743A1 (en) | 2004-03-30 | 2005-03-28 | Synthesis of pyrrole-2-carbonitriles |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012101507A Division JP2012158599A (ja) | 2004-03-30 | 2012-04-26 | ピロール−2−カルボニトリルの合成 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007531748A true JP2007531748A (ja) | 2007-11-08 |
JP5068642B2 JP5068642B2 (ja) | 2012-11-07 |
Family
ID=34963600
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007506458A Expired - Fee Related JP5068642B2 (ja) | 2004-03-30 | 2005-03-28 | ピロール−2−カルボニトリルの合成 |
JP2012101507A Withdrawn JP2012158599A (ja) | 2004-03-30 | 2012-04-26 | ピロール−2−カルボニトリルの合成 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012101507A Withdrawn JP2012158599A (ja) | 2004-03-30 | 2012-04-26 | ピロール−2−カルボニトリルの合成 |
Country Status (22)
Country | Link |
---|---|
US (1) | US7399870B2 (ja) |
EP (1) | EP1730109B1 (ja) |
JP (2) | JP5068642B2 (ja) |
KR (1) | KR20070009654A (ja) |
AR (1) | AR049157A1 (ja) |
AT (1) | ATE402145T1 (ja) |
AU (1) | AU2005230896A1 (ja) |
BR (1) | BRPI0509317B1 (ja) |
CA (1) | CA2560964C (ja) |
CR (1) | CR8641A (ja) |
DE (1) | DE602005008408D1 (ja) |
DK (1) | DK1730109T3 (ja) |
EC (1) | ECSP066897A (ja) |
ES (1) | ES2310817T3 (ja) |
HN (1) | HN2005000134A (ja) |
IL (1) | IL178184A0 (ja) |
NO (1) | NO20064891L (ja) |
PE (1) | PE20060203A1 (ja) |
PL (1) | PL1730109T3 (ja) |
RU (1) | RU2006134013A (ja) |
TW (1) | TW200604166A (ja) |
WO (1) | WO2005097743A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012188380A (ja) * | 2011-03-10 | 2012-10-04 | Meiji Univ | 芳香族へテロ環化合物のニトリル化法 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2008341138A1 (en) * | 2007-12-20 | 2009-07-02 | Teva Women's Health, Inc. | Dosage regimens and pharmaceutical compositions and packages for emergency contraception |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3506642A1 (de) * | 1985-02-26 | 1986-08-28 | A. Nattermann & Cie GmbH, 5000 Köln | Neue pyrrolamidine, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5204332A (en) * | 1988-12-05 | 1993-04-20 | American Cyanamid Company | Pyrrole carbonitrile and nitropyrrole insecticidal and acaricidal and molluscicidal agents |
KR20000047461A (ko) * | 1998-12-29 | 2000-07-25 | 성재갑 | 트롬빈 억제제 |
-
2005
- 2005-03-22 US US11/086,061 patent/US7399870B2/en not_active Expired - Fee Related
- 2005-03-28 PL PL05729200T patent/PL1730109T3/pl unknown
- 2005-03-28 DK DK05729200T patent/DK1730109T3/da active
- 2005-03-28 WO PCT/US2005/010468 patent/WO2005097743A1/en active Application Filing
- 2005-03-28 EP EP05729200A patent/EP1730109B1/en active Active
- 2005-03-28 BR BRPI0509317-1A patent/BRPI0509317B1/pt not_active IP Right Cessation
- 2005-03-28 AT AT05729200T patent/ATE402145T1/de not_active IP Right Cessation
- 2005-03-28 DE DE602005008408T patent/DE602005008408D1/de active Active
- 2005-03-28 AU AU2005230896A patent/AU2005230896A1/en not_active Withdrawn
- 2005-03-28 KR KR1020067022663A patent/KR20070009654A/ko not_active Application Discontinuation
- 2005-03-28 JP JP2007506458A patent/JP5068642B2/ja not_active Expired - Fee Related
- 2005-03-28 RU RU2006134013/04A patent/RU2006134013A/ru not_active Application Discontinuation
- 2005-03-28 CA CA2560964A patent/CA2560964C/en not_active Expired - Fee Related
- 2005-03-28 ES ES05729200T patent/ES2310817T3/es active Active
- 2005-03-30 PE PE2005000364A patent/PE20060203A1/es not_active Application Discontinuation
- 2005-03-30 AR ARP050101206A patent/AR049157A1/es unknown
- 2005-03-30 TW TW094109918A patent/TW200604166A/zh unknown
- 2005-03-30 HN HN2005000134A patent/HN2005000134A/es unknown
-
2006
- 2006-09-19 IL IL178184A patent/IL178184A0/en unknown
- 2006-09-20 CR CR8641A patent/CR8641A/es not_active Application Discontinuation
- 2006-09-29 EC EC2006006897A patent/ECSP066897A/es unknown
- 2006-10-26 NO NO20064891A patent/NO20064891L/no not_active Application Discontinuation
-
2012
- 2012-04-26 JP JP2012101507A patent/JP2012158599A/ja not_active Withdrawn
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3506642A1 (de) * | 1985-02-26 | 1986-08-28 | A. Nattermann & Cie GmbH, 5000 Köln | Neue pyrrolamidine, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012188380A (ja) * | 2011-03-10 | 2012-10-04 | Meiji Univ | 芳香族へテロ環化合物のニトリル化法 |
Also Published As
Publication number | Publication date |
---|---|
AR049157A1 (es) | 2006-07-05 |
PL1730109T3 (pl) | 2008-10-31 |
BRPI0509317A (pt) | 2007-09-04 |
JP5068642B2 (ja) | 2012-11-07 |
AU2005230896A1 (en) | 2005-10-20 |
RU2006134013A (ru) | 2008-05-10 |
NO20064891L (no) | 2006-10-26 |
US7399870B2 (en) | 2008-07-15 |
US20050222432A1 (en) | 2005-10-06 |
EP1730109B1 (en) | 2008-07-23 |
ECSP066897A (es) | 2006-11-24 |
PE20060203A1 (es) | 2006-03-30 |
TW200604166A (en) | 2006-02-01 |
KR20070009654A (ko) | 2007-01-18 |
CA2560964C (en) | 2012-10-30 |
HN2005000134A (es) | 2007-03-26 |
DE602005008408D1 (en) | 2008-09-04 |
BRPI0509317B1 (pt) | 2014-04-29 |
ATE402145T1 (de) | 2008-08-15 |
EP1730109A1 (en) | 2006-12-13 |
WO2005097743A1 (en) | 2005-10-20 |
CA2560964A1 (en) | 2005-10-20 |
JP2012158599A (ja) | 2012-08-23 |
ES2310817T3 (es) | 2009-01-16 |
IL178184A0 (en) | 2006-12-31 |
CR8641A (es) | 2007-08-28 |
DK1730109T3 (da) | 2008-09-29 |
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