Reaktion #11666

Reaktionsgleichung

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle