Reacción #43836

ord-9b49e2a1877e4598b9f303feb4a4778c

Ecuación de reacción

BrCCCOc1ccccc1
3-Phenoxypropyl bromide
O=C([O-])[O-].[K+].[K+]
K2CO3
CCCc1nc2cc(NS(=O)(=O)c3ccc(F)cc3)ccc2n1CC(=O)OC(C)(C)C
[5-(4-fluoro-benzenesulfonylamino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester
→
CCCc1nc2cc(N(CCCOc3ccccc3)S(=O)(=O)c3ccc(F)cc3)ccc2n1CC(=O)OC(C)(C)C
{5-[(4-Fluoro-benzenesulfonyl)-(3-phenoxy-propyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid tert-butyl ester

Reactantes

BrCCCOc1ccccc1
3-Phenoxypropyl bromide
O=C([O-])[O-].[K+].[K+]
K2CO3
CCCc1nc2cc(NS(=O)(=O)c3ccc(F)cc3)ccc2n1CC(=O)OC(C)(C)C
[5-(4-fluoro-benzenesulfonylamino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester

Reactivos

Ninguno

Disolventes

CCOC(C)=O
EtOAc
O
H2O
CC#N
CH3CN

Condiciones de reacción

Temperatura
80°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Filtraciónfiltered through an Extrelut column

Procedimiento

3-Phenoxypropyl bromide (0.27 mmol) and K2CO3 (63 mg, 0.45 mmol) were added to a solution of [5-(4-fluoro-benzenesulfonylamino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester (40 mg, 0.09 mmol) in CH3CN (1 mL), and stirred overnight at 80° C. The reaction mixture was diluted with EtOAc and H2O, and then filtered through an Extrelut column.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07732618B2uspto-grants-2010_06