Réaction #1509622

Équation de réaction

2-amino-4-(3-isobutylcarbamoyl-propyl)-imidazole-1-carboxylic acid tert-butyl ester

dichloromethane

TFA

→

compound 8

Rendement 97.0%

4-(2-amino-1H-imidazol-4-yl)-N-isobutyl-butyramide hydrochloride

Rendement 97.0%

Conditions de réaction

Traitement

1. 1
   AutreAfter that time the reaction was evaporated to dryness and toluene (2 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   ConcentrationAgain the mixture was concentrated
4. 4
   workup.DISSOLUTIONThe resulting TFA salt was dissolved in dichloromethane (1 mL)
5. 5
   workup.ADDITION2M HCl in diethyl ether (0.50 mL) was added
6. 6
   Filtrationwas collected by filtration
7. 7
   Lavagewashed with diethyl ether (3 mL)

Mode opératoire

A solution of 2-amino-4-(3-isobutylcarbamoyl-propyl)-imidazole-1-carboxylic acid tert-butyl ester 23 (76 mg, 0.234 mmol) in anhydrous dichloromethane (1 mL) was cooled to 0° C. TFA (1 mL) was charged into the flask and the reaction stirred for 5 h. After that time the reaction was evaporated to dryness and toluene (2 mL) was added. Again the mixture was concentrated and the process repeated. The resulting TFA salt was dissolved in dichloromethane (1 mL) and 2M HCl in diethyl ether (0.50 mL) was added followed by cold diethyl ether (8 mL) The precipitate was collected by filtration and washed with diethyl ether (3 mL) to yield the target compound 8 (59 mg, 97%) as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 12.14 (s, 1H), 11.70 (s, 1H), 7.89 (m, 1H), 7.34 (br s, 2H), 6.55 (s, 1H), 2.84 (t, 2H, J=6.6 Hz), 2.38 (t, 2H, J=7.5 Hz), 2.10 (t, 2H, J=7.5 Hz), 1.60-1.79 (m, 3H), 0.82 (d, 6H, J=6.3 Hz); 13C NMR (75 MHz, DMSO-d6) δ 171.52, 146.78, 126.31, 108.68, 46.00, 34.41, 28.09, 23.94, 23.64, 20.18; HRMS (ESI) calcd for C11H21N4O (MH)+ 225.1709, found 225.1711.

Source