Diisopropylethylamine → HCID 178479467, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-3-{[7-(3-amino-propoxy)-4-oxo-4H-quinolizine-2-carbonyl]-amino}-2-benzenesulfonylamino-propionic acid trifluoroacecic acid salt (compound XIV)(15 mg, 0.025 mmol), diisopropylethylamine (13 μl, 0.075 mmol) and 1H-pyrazole-1-carboxamidine hydrochloride (6 mg, 0.038 mmol) in DMF (0.5 ml) and water (0.5 ml) was stirred at 60° C. for 7 hours. It was then concentrated and the residue was flash chromatographed (ethanol:NH4OH:water; 8:1:1) and lyophilized in a (1:1) mixture of 0.1N HCl and water to afford 11.4 mg of pure desired product as a yellow solid which was characterized by 1HNMR (400 MHz, CD3OD) δ: 2.14-2.21 (m, 2H), 3.44-3.48 (m,2H), 3.49-3.54 (dd, J=13.5 and 9.0 Hz, 1H), 3.77-3.82 (dd, J=13.5 and 5.0 Hz, 1H), 4.23-4.28 (m, 3H), 6.94 (d, J=1.5 Hz, 1H), 7.37 (s, 1H), 7.43-7.56 (m, 4H), 7.85-7.86 (m, 2H), 7.91 (d, J=9.5 Hz, 1H), 8.7 (s, 1H).

Provenance & Evidence