GB858086A - Method for synthesis of amides of imidazoles or benzimidazoles - Google Patents

Method for synthesis of amides of imidazoles or benzimidazoles

Info

Publication number
GB858086A
GB858086A GB31557/59A GB3155759A GB858086A GB 858086 A GB858086 A GB 858086A GB 31557/59 A GB31557/59 A GB 31557/59A GB 3155759 A GB3155759 A GB 3155759A GB 858086 A GB858086 A GB 858086A
Authority
GB
United Kingdom
Prior art keywords
reacted
ethyl
product subsequently
groups
dicarbonyldiimidazole
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.)
Expired
Application number
GB31557/59A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB858086A publication Critical patent/GB858086A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Landscapes

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

Abstract

Amides of the formula: <FORM:0858086/IV(b)/1> are prepared by reacting in an inert, substantially dry liquid medium a carboxylic acid of the formula: <FORM:0858086/IV(b)/2> with an N : N1-carbonyldiimidazole of the formula: <FORM:0858086/IV(b)/3> wherein A-C is a carboxylic acid radical which is free from other groups capable of reacting with the N : N1-carboxyldiimidazole reactant and I is a substituted or unsubstituted imidazole or benzimidazole bonded through a nitrogen atom of the heterocyclic azole ring. The process is particularly applicable to the use as carboxylic acid reactants of aminoacids and peptides in which the amino groups have been acylated, e.g. with carbobenzoxy, tertiarybutyloxycarbonyl or phthaloyl groups. The amide products may be further reacted separately or in situ with an amine to form an amide corresponding to the amine reactant, examples of the latter being aminoacids or peptides in which free carboxyl groups are blocked by metal ions or esterifying groups. In Examples (1) carbobenzoxyglycine is reacted with N : N1-dicarbonyldiimidazole and the product subsequently reacted with ethyl-L-tyrosinate, ethyl-DL-phenylalaninate, the sodium salts of L- and DL-phenylalanine, ethyl-L-leucinate and ethyl glycinate ; (2) carbobenzoxyglycine is reacted with N : N1-dicarbanyldibenzimidazole and the product subsequently reacted with ethyl-DL-phenylalaninate ; (3) tertiary butyloxycarbonyl-L-phenylalanine is reacted with N : N1-dicarbonyldiimidazole and the product subsequently reacted with ethyl glycinate ; (4) phthaloyl-DL-phenylalanine is reacted with N : N1-dicarbonyldiimadazole and the product subsequently reacted with ethyl glycylglycinate ; and (5) carbobenzoxy-L-alanine is reacted with N : N1-dicarbonyldiimidazole and the product subsequently reacted with ethyl glycinate. N N1-carbonyldibenzimidazole is prepared by passing phosgene through a benzene solution of benzimidazole.
GB31557/59A 1958-09-16 1959-09-16 Method for synthesis of amides of imidazoles or benzimidazoles Expired GB858086A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US858086XA 1958-09-16 1958-09-16

Publications (1)

Publication Number Publication Date
GB858086A true GB858086A (en) 1961-01-04

Family

ID=22194088

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31557/59A Expired GB858086A (en) 1958-09-16 1959-09-16 Method for synthesis of amides of imidazoles or benzimidazoles

Country Status (1)

Country Link
GB (1) GB858086A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007005972A1 (en) * 2005-06-30 2007-01-11 Celgene Corporation Processes for the preparation of 4-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione compounds

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007005972A1 (en) * 2005-06-30 2007-01-11 Celgene Corporation Processes for the preparation of 4-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione compounds
US7994327B2 (en) 2005-06-30 2011-08-09 Celgene Corporation Processes for the preparation of 4-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione compounds
EP2380887A1 (en) * 2005-06-30 2011-10-26 Celgene Corporation Processes for the preparation of 4-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione compounds
US8785644B2 (en) 2005-06-30 2014-07-22 Celgene Corporation Processes for the preparation of 4-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione compounds
US9394274B2 (en) 2005-06-30 2016-07-19 Celgene Corporation Processes for the preparation of 4-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione compounds
US9822093B2 (en) 2005-06-30 2017-11-21 Celgene Corporation Processes for the preparation of 4-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione compounds
US10266514B2 (en) 2005-06-30 2019-04-23 Celgene Corporation Processes for the preparation of 4-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione compounds

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