Diisopropylethylamine → HCID 86296367, compound

Participants

Reaction Steps

In a 40 mL vial isopropyl (2-(5-amino-2-chlorophenyl)imidazo[1,2-a]pyrimidin-6-yl)carbamate (I-9) (30 mg, 0.09 mmol) was dissolved in DMF (Volume: 0.3 mL). 5-fluorofuran-2-carboxylic acid (11 mg, 0.09 mmol) was then added to the reaction mixture followed by HATU (65.98 mg, 0.17 mmol) and (iPr)2NEt (0.043 mL, 0.26 mmol). The reaction was stirred at rt for 8 hrs. The reaction was monitored was LCMS which indicated the reaction was complete with a new peak of desired mass was observed (M+H=468.1). The reaction mixture was quenched with water and extracted with ethyl acetate (3×5 mL). Combined all organics, dried over sodium sulfate and concentrated under reduce pressure. The crude reaction purified by reverse phase HPLC yeild 2-(2-chloro-5-(5-fluorofuran-2-carboxamido)phenyl)imidazo[1,2-a]pyrimidin-6-yl)carbamate (1). The TFA salt was neutralized to a free base by a HCO3 column. 1H NMR (400 MHz, DMSO) δ 10.41 (s, 1H), 10.01 (s, 1H), 9.31 (s, 1H), 8.69 (s, 1H), 8.61 (d, J=2.7, 1H), 8.51 (d, J=2.7, 1H), 7.87 (dd, J=2.7, 8.8, 1H), 7.53 (d, J=8.7, 1H), 7.47 (t, J=3.6, 1H), 6.11 (dd, J=3.7, 7.1, 1H), 5.03-4.85 (m, 1H), 1.29 (d, J=6.2, 6H). M/Z=(458.1M+1). RT=1.64 min.

Provenance & Evidence