L-Lactic Acid → HCID 178462374, compound

Participants

Reaction Steps

To a solution of 2,4-diamino-5-chloro-N-(N-{4-[4-(2,3-dihydroxypropoxy)naphthalen-1-yl]butyl}carbamimidoyl)benzamide (24, 28 mg, 0.06 mmole) in EtOH (10 mL) was added L-(+)-lactic acid (5.20 mg, 0.06 mmole) at room temperature and the reaction mixture was stirred for 15 min. The solution was concentrated and the residue was azeotroped with MeOH. The residue was dissolved in H2O (3 mL) and lyophilized to afford lactic acid salt 26 (28 mg, 84%) as a yellow solid: mp 115-118° C.; 1H NMR (300 MHz, CD3OD) δ 8.32 (d, J=8.4 Hz, 1H), 8.01 (d, J=8.4 Hz, 1H), 7.53 7.40 (m, 2H), 7.24 (d, J=7.8 Hz, 1H), 6.83 (d, J=7.8 Hz, 1H), 4.21 4.10 (m, 3H), 4.01-3.94 (m, 1H), 3.82-3.73 (m, 2H), 3.35-3.33 (m, 2H), 3.08 (t, J=7.0, Hz, 1H), 1.89-1.77 (m, 4H), 1.31 (d, J=7.0 Hz, 3H); ESI-MS m/z 524 [C23H28ClN7O4+H]+.

Provenance & Evidence