Diisopropylethylamine → HCID 178513012, compound

Participants

Reaction Steps

4-(2-Amino-ethoxy)-1-benzopyran-2-one trifluoroacetate (0.313 mmol, 100 mg) is placed in a small vial along with 2 mL of acetonitrile. Diisopropylethylamine is added dropwise until the pH of the solution is ˜9 by pH paper. N,N′-Bis(tert-butoxycarbonyl)-1-H-pyrazole-1-carboxamidine (0.24 mmol, 74.5 mg) is added and the reaction is mixed at ambient temperature for 5 hrs. The reaction mixture is concentrated in vacuo, then is redissolved in neat TFA and is stirred at ambient temperature for 30 min. The TFA is removed under reduced pressure and the residue is purified by reversed-phase HPLC to afford the title compound as the trifluoroacetic acid salt (35.0 mg, 31%). 1H NMR (DMSO-d6, 300 MHz) δ 7.88 (1H, dd, J=1.5, 8 Hz), 7.81 (1H, br t), 7.68 (1H, m), 7.39 (2H, m), 7.28 (3H, br s), 5.49 (1H, s), 4.30 (2H, t, J=5 Hz), 3.67 (2H, q, J=5.5 Hz); MS (ESI, Pos.) calcd for C12H13N3O3 m/z [M+H]=248.1, found 248.1.

Provenance & Evidence