Réaction #1269852

ord-562e7c56b4b346a3940ce6373b743d87

Équation de réaction

CCOC(=O)N1CCN(C(=O)CN)CC1
4-(2-amino-acetyl)-piperazine-1-carboxylic acid ethyl ester
O=C(O)c1csc(-c2ccccc2)n1
2-phenyl-1,3-thiazole-4-carboxylic acid
CCN(C(C)C)C(C)C
DIPEA
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU
CCOC(=O)N1CCN(C(=O)CNC(=O)c2csc(-c3ccccc3)n2)CC1
desired product
Rendement 49.0%
CCOC(=O)N1CCN(C(=O)CNC(=O)c2csc(-c3ccccc3)n2)CC1
4-{2-[(2-Phenyl-thiazole-4-carbonyl)-amino]-acetyl}-piperazine-1-carboxylic acid ethyl ester
Rendement 49.0%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autrethe reaction mixture was directly purified by preparative HPLC (IV)

Mode opératoire

To a solution of 2-phenyl-1,3-thiazole-4-carboxylic acid (5.1 mg) and DIPEA (3 eq) in DMF (0.4 mL) was added TBTU (1.2 eq) in DMF (0.2 mL). Then, a solution of 4-(2-amino-acetyl)-piperazine-1-carboxylic acid ethyl ester (5.4 mg, prepared as described in WO2006114774) in DMF (0.2 mL) was added. After stirring overnight at RT, the reaction mixture was directly purified by preparative HPLC (IV) to give 4.9 mg of the desired product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08664203B2uspto-grants-2014_03