Reacción #1596971

ord-6b5c7f22a4c84dd6a43f8b48743d0283

Ecuación de reacción

CC(C)(C)OC(=O)CN(CCCCCC(=O)O)Cc1ccccn1
6-((2-tert-butoxy-2-oxoethyl)(pyridin-2-ylmethyl)amino)hexanoic acid
Nc1ccc(S(N)(=O)=O)cc1
sulfanilamide
CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HATU
→
CC(C)(C)OC(=O)CN(CCCCCC(=O)Nc1ccc(S(N)(=O)=O)cc1)Cc1ccccn1
tert-butyl 2-((6-oxo-6-(4-sulfamoylphenylamino)hexyl)(pyridin-2-ylmethyl)amino)acetate
Rendimiento 31.0%

Reactantes

CC(C)(C)OC(=O)CN(CCCCCC(=O)O)Cc1ccccn1
6-((2-tert-butoxy-2-oxoethyl)(pyridin-2-ylmethyl)amino)hexanoic acid
Nc1ccc(S(N)(=O)=O)cc1
sulfanilamide
CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HATU

Reactivos

Ninguno

Disolventes

CN(C)C=O
DMF
CCN(CC)CC
Et3N

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe reaction mixture was purified by flash chromatography over silica gel eluting with MeOH/DCM

Procedimiento

A solution of 6-((2-tert-butoxy-2-oxoethyl)(pyridin-2-ylmethyl)amino)hexanoic acid (0.6545 g, 1.95 mmol), sulfanilamide (0.362 g, 2.10 mmol) and HATU (0.798 g, 2.10 mmol) in DMF (10 mL) and Et3N (1.0 mL) was stirred at 40° C. overnight. The reaction mixture was purified by flash chromatography over silica gel eluting with MeOH/DCM to give tert-butyl 2-((6-oxo-6-(4-sulfamoylphenylamino)hexyl)(pyridin-2-ylmethyl)amino)acetate (297 mg, 31%). ESMS m/z: 491.3 (M+H)+.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08211402B2uspto-grants-2012_07