Reacción #1269852

ord-562e7c56b4b346a3940ce6373b743d87

Ecuación de reacción

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
Rendimiento 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
Rendimiento 49.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

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

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08664203B2uspto-grants-2014_03