Trifluoroacetic acid → HCID 45789378, compound

Participants

Reaction Steps

To a solution of tert-butylN-{[2-(dimethylamino)-7-iodo-1,3-benzoxazol-5-yl]methyl}carbamate (120 mg, 0.29 mmol) in 4 ml of CH2Cl2 was added slowly 0.5 mL of trifluoroacetic acid and it was stirred at room temperature for 30 min. The excess of TFA was removed under vacuum. The product was purified by column chromatography (CH2Cl2/MeOH 9:1) yielding 64 mg (70%) of N2,N2-dimethyl-5-(aminomethyl)-7-iodo-1,3-benzoxazol-2-amine as a white solid. 1H NMR (CD3OD) δ 7.46 (d, 1H, J=1.5 Hz, H-6); 7.30 (d, 1H, J=1.5 Hz, H-4); 4.12 (s, 2H, CH2); 3.23, 3.24 (s, 6H, CH3×2); 13C NMR (CD3OD) δ 164.5 (C-2), 152.7 (C-7a), 144.6 (C-3a), 132.9 (C-5), 131.6 (C-6), 117.3 (C-4), 72.0 (C-7), 44.2 (CH2), 38.3 (CH3).

Provenance & Evidence