Efficient synthesis of heterocyclic neurotensin receptor ligands by microwave-assisted aminocarbonylation

Synthesis (Germany)

Volumn 45, Issue 17, 2013, Pages 2474-2480

  Lang, Christopher ^a   Gmeiner, Peter ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

aminocarbonylation; aryl bromide; medicinal chemistry; microwave; palladacycles; palladium catalysis

Indexed keywords

AMINOCARBONYLATION; ARYL BROMIDES; MEDICINAL CHEMISTRY; PALLADACYCLES; PALLADIUM CATALYSIS;

MICROWAVES; REACTION KINETICS;

ORGANIC COMPOUNDS;

1 (4 BROMO 2 ISOPROPHYPHENYL) 5 (2,6 DIMETHOXYPHENYL) 1H PYRAZOLE 3 CARBOXYLIC ACID; 2 [5 (2,6 DIMETHOXYPHENYL) 1 [4 [N (3 DIMETHYLAMINOPROPYL) N METHYLCARBAMOYL] 2 ISOPROPYLPHENYL] 1H PYRAZOL 3 YLCARBONYLAMINO]ADAMANTANE 2 CARBOXYLIC ACID; 2 [[[1 (4 BROMO 2 ISOPROPYLPHENYL) 5 (2,6 DIMETHOXYPHENYL)1H PYRAZOL 3 YL]CARBONYL]AMINO]ADAMANTANE 2 CARBOXYLIC ACID; 2 [[[5 (2,6 DIMETHOXYPHENYL) 1 [2 ISOPROPYL 4 [[METHYL [ 3 (METHYLAMINO)PROPYL]AMINO]CARBONYL]PHENYL] 1H PYRAZOL 3 YL]CARBONYL]AMINO]ADAMANTANE 2 CARBOXYLIC ACID; 2 [[[5 (2,6 DIMETHOXYPHENYL) 1 [4 [(DIMETHYLAMINO)CARBONYL] 2 ISOPROPYLPHENYL] 1H PYRAZOL 3 YL]CARBONYL]AMINO]ADAMANTANE 2 CARBOXYLIC ACID; 2 [[[5 (2,6 DIMETHOXYPHENYL) 1 [4 [(HEPTYLAMINO)CARBONYL] 2 ISOPROPYLPHENYL] 1H PYRAZOL 3 YL]CARBONYL]AMINO]ADAMANTANE 2 CARBOXYLIC ACID; 2 [[[5 (2,6 DIMETHOXYPHENYL) 1 [4 [[[3 (DIMETHYLAMINO)PROPYL](METHYL)AMINO]CARBONYL] 2 ISOPROPYLPHENYL] 1H PYRAZOL 3 YL]CARBONYL]AMINO]ADAMANTANE 2 CARBOXYLIC ACID; 4 BROMO 2 ISOPROPYLANILINE; 5 (2,6 DIMETHOXYPHENYL) 1 [4 [[[3 (DIMETHYLAMINO)PROPYL](METHYL)AMINO]CARBONYL] 2 ISOPROPYLPHENYL] 1H PYRAZOLE 3 CARBOXYLIC ACID; DI TERT BUTYL N [[5 (2,6 DIMETHOXYPHENYL) 1 [4 [[[3 (DIMETHYLAMINO)PROPYL](METHYL)AMINO]CARBONYL] 2 ISOPROPYLPHENYL] 1H PYRAZOL 3 YL]CARBONYL]GLUTAMIC ACID; METHYL 1 (4 BROMO 2 ISOPROPYLPHENYL) 5 (2,6 DIMETHOXYPHENYL) 1H PYRAZOLE 3 CARBOXYLIC ACID; METHYL 5 (2,6 DIMETHOXYPHENYL) 1 [4 [[[3 (DIMETHYLAMINO)PROPYL](METHYL)AMINO]CARBONYL] 2 ISOPROPYLPHENYL] 1H PYRAZOLE 3 CARBOXYLIC ACID; N [[1 (4 BROMO 2 ISOPROPYLPHENYL) 5 (2,6 DIMETHOXYPHENYL) 1H PYRAZOL 3 YL]CARBONYL]LEUCINE; N [[5 (2,6 DIMETHOXYPHENYL) 1 [4 [[[3 (DIMETHYLAMINO)PROPYL](METHYL)AMINO]CARBONYL] 2 ISOPROPYLPHENYL] 1H PYRAZOL 3 YL]CARBONYL]GLUTAMIC ACID; N [[5 (2,6 DIMETHOXYPHENYL) 1 [4 [[[3 (DIMETHYLAMINO)PROPYL](METHYL)AMINO]CARBONYL] 2 ISOPROPYLPHENYL] 1H PYRAZOL 3 YL]CARBONYL]LEUCINE; N [[5 (2,6 DIMETHOXYPHENYL) 1 [4 [[[3 (DIMETHYLAMINO)PROPYL](METHYL)AMINO]CARBONYL] 2 ISOPROPYLPHENYL] 1H PYRAZOL 3 YL]CARBONYL]PHENYLALANINE; N [[5 (2,6 DIMETHOXYPHENYL) 1 [4 [[[3 (DIMETHYLAMINO)PROPYL](METHYL)AMINO]CARBONYL] 2 ISOPROPYLPHENYL] 1H PYRAZOL 3 YL]CARBONYL]TYROSINE; N [[5 (2,6 DIMETHOXYPHENYL) 1 [4 [[[3 (DIMETHYLAMINO)PROPYL](METHYL)AMINO]CARBONYL] 2 ISOPROPYLPHENYL] 1H PYRAZOL 3 YL]CARBONYL]VALINE; TERT BUTYL N [[1 (4 BROMO 2 ISOPROPYLPHENYL) 5 (2,6 DIMETHOXYPHENYL) 1H PYRAZOL 3 YL]CARBONYL]LEUCINATE; TERT BUTYL N [[5 (2,6 DIMETHOXYPHENYL) 1 [4 [[[3 (DIMETHYLAMINO)PROPYL](METHYL)AMINO]CARBONYL] 2 ISOPROPYLPHENYL] 1H PYRAZOL 3 YL]CARBONYL]PHENYLALANINATE; TERT BUTYL N [[5 (2,6 DIMETHOXYPHENYL) 1 [4 [[[3 (DIMETHYLAMINO)PROPYL](METHYL)AMINO]CARBONYL] 2 ISOPROPYLPHENYL] 1H PYRAZOL 3 YL]CARBONYL]VALINATE; TERT BUTYL O (TERT BUTYL) N [[5 (2,6 DIMETHOXYPHENYL) 1 [4 [[[3 (DIMETHYLAMINO)PROPYL](METHYL)AMINO]CARBONYL] 2 ISOPROPYLPHENYL] 1H PYRAZOL 3 YL]CARBONYL]TYROSINATE; UNCLASSIFIED DRUG;

AMINOCARBONYLATION; ARTICLE; CARBONYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; MICROWAVE RADIATION; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 84883133829     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0033-1338497     Document Type: Article

References (11)

1. Myers R. M., Shearman J. W., Kitching M. O., Ramos-Montoya A., Neal D. E., Ley S. V. ACS Chem. Biol.: 2009; 4 503
2. Griebel G., Holsboer F. Nat. Rev. Drug Discov.: 2012; 11 462
3. Battilocchio C., Deadman B. J., Nikbin N., Kitching M. O., Baxendale I. R., Ley S. V. Chem. Eur. J.: 2013; 19 2013
4. Schoenberg A., Heck R. F. J. Org. Chem.: 1974; 39 3327
5. Roy S., Roy S., Gribble G. W. Tetrahedron: 2012; 68 9867
6. Kaiser N. F. K, Hallberg A., Larhed M. J. Comb. Chem.: 2002; 4 109
7. Wannberg J., Larhed M. J. Org. Chem.: 2003; 68 5750
8. Wu X. Y., Larhed M. Org. Lett.: 2005; 7 3327
9. Wu X. Y., Ekegren J. K. Larhed M. Organometallics: 2006; 25 1434
10. Christmann U., Vilar R. Angew. Chem. Int. Ed.: 2005; 44 366
11. Galardon E., Ramdeehul S., Brown J. M., Cowley A., Hii K. K., Jutand A. Angew. Chem. Int. Ed.: 2002; 41 1760