Reacción #11666

Ecuación de reacción

1,1′-carbonyldiimidazol

{2-[(5-Aminomethyl-thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester

trifluoroacetic acid

NaHCO3

→

5-[(3-Prop-2-ynyl-ureido)-methyl]-thiophene-2-carboxylic acid (2-amino-phenyl)-amide

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added carefully
2. 2
   Extracciónthe aqueous phase was extracted three times with ethyl acetate
3. 3
   SecadoThe combined organic phases were dried over Na2SO4
4. 4
   Otrothe solvent was evaporated
5. 5
   OtroThe residue was purified by HPLC/MS

Procedimiento

To a solution of 15.8 mg (0.288 mmol) in 1 ml THF were added 46.7 mg (0.288 mmol) 1,1′-carbonyldiimidazol. After 1 h at rt 100 mg (0.288 mmol) {2-[(5-Aminomethyl-thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester were added and the reaction mixture was stirred for 1 h at rt. 1.7 ml trifluoroacetic acid were added and after 16 h at rt sat. aqueous NaHCO3 was added carefully and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over Na2SO4 and the solvent was evaporated. The residue was purified by HPLC/MS to yield 75 mg (0.228 mmol 5-[(3-Prop-2-ynyl-ureido)-methyl]-thiophene-2-carboxylic acid (2-amino-phenyl)-amide; exact MW [M+H] calc'd: 329.11; MW found [M+H]: 329.3.

Fuente