Toluene → heptanoic acid [4-(2-amino-3H-imidazol-4-yl)phenyl]amide hydrochloride

Participants

Reaction Conditions

Reaction Steps

2-amino-5-(4-heptanoylaminophenyl)imidazole-1-carboxylic acid tert-butyl ester (0.089 g, 0.230 mmol) was dissolved in anhydrous dichloromethane (5 mL) and cooled to 0° C. Trifluoroacetic acid (0.50 mL) was added drop-wise while the reaction continued to stir at 0° C. Upon completion, the reaction was allowed to warm to room temperature over the course of 12 h. Toluene (2 mL) was added and the reaction was evaporated to dryness. The crude TFA salt was then dissolved in dichloromethane (3 mL) and a 2M solution of HCl in diethyl ether (0.10 mL) was added. The solution was again concentrated under reduced pressure and the resulting product triturated with cold diethyl ether (5 mL) to afford 0.072 g (97%) of the desired compound heptanoic acid [4-(2-amino-3H-imidazol-4-yl)phenyl]amide in its corresponding hydrochloride form as a yellow amorphous solid: 1H NMR (300 MHz, DMSO-d6) δ 12.80 (s, 1H), 12.05 (s, 1H), 10.08 (s, 1H), 7.67 (d, 2H, J=8.1 Hz), 7.59 (d, 2H, J=8.1 Hz), 7.43 (br s, 2H), 7.27 (s, 1H), 2.31 (t, 2H, J=6.8 Hz), 1.58 (m, 2H), 1.27 (m, 6H), 0.86 (t, 3H, J=5.7 Hz); 13C NMR (75 MHz, DMSO-d6) δ 172.1, 148.2, 139.8, 127.1, 125.4, 123.0, 119.9, 109.1, 37.1, 31.7, 29.0, 25.7, 22.7, 14.6; HRMS (ESI) calcd for C16H22N4O (M+) 286.1794. found 286.1788.

Provenance & Evidence