GB858086A - Method for synthesis of amides of imidazoles or benzimidazoles - Google Patents
Method for synthesis of amides of imidazoles or benzimidazolesInfo
- 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
Links
- 150000001408 amides Chemical class 0.000 title abstract 4
- 150000002460 imidazoles Chemical class 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 150000001556 benzimidazoles Chemical class 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 abstract 3
- 239000000376 reactant Substances 0.000 abstract 3
- ZHLKFJCNKZEBNG-UHFFFAOYSA-N 2-(ethylamino)-3-phenylpropanoic acid Chemical compound CCNC(C(O)=O)CC1=CC=CC=C1 ZHLKFJCNKZEBNG-UHFFFAOYSA-N 0.000 abstract 2
- CJUMAFVKTCBCJK-UHFFFAOYSA-N N-benzyloxycarbonylglycine Chemical compound OC(=O)CNC(=O)OCC1=CC=CC=C1 CJUMAFVKTCBCJK-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 229940024606 amino acid Drugs 0.000 abstract 2
- 235000001014 amino acid Nutrition 0.000 abstract 2
- 150000001413 amino acids Chemical class 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- -1 carboxylic acid radical Chemical class 0.000 abstract 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Chemical compound OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 abstract 2
- 102000004196 processed proteins & peptides Human genes 0.000 abstract 2
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- QIGLJVBIRIXQRN-ZETCQYMHSA-N ethyl (2s)-2-amino-4-methylpentanoate Chemical compound CCOC(=O)[C@@H](N)CC(C)C QIGLJVBIRIXQRN-ZETCQYMHSA-N 0.000 abstract 1
- LFAVEINQLWIXRA-UHFFFAOYSA-N ethyl 2-[(2-aminoacetyl)amino]acetate Chemical compound CCOC(=O)CNC(=O)CN LFAVEINQLWIXRA-UHFFFAOYSA-N 0.000 abstract 1
- SBBWEQLNKVHYCX-JTQLQIEISA-N ethyl L-tyrosinate Chemical compound CCOC(=O)[C@@H](N)CC1=CC=C(O)C=C1 SBBWEQLNKVHYCX-JTQLQIEISA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229910021645 metal ion Inorganic materials 0.000 abstract 1
- TYRGLVWXHJRKMT-QMMMGPOBSA-N n-benzyloxycarbonyl-l-serine-betalactone Chemical compound OC(=O)[C@H](C)NC(=O)OCC1=CC=CC=C1 TYRGLVWXHJRKMT-QMMMGPOBSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229960005190 phenylalanine Drugs 0.000 abstract 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
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.
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)
| 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 |
-
1959
- 1959-09-16 GB GB31557/59A patent/GB858086A/en not_active Expired
Cited By (7)
| 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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