Hydrochloric Acid → HCID 58574661, compound

Participants

Reaction Steps

To a solution of the acid prepared from Example 28.1b and EDCI-HCl (80.2 mg, 0.42 mmol) in DCM (10 mL) was added 5-methylthiazol-2-amine (25.5 mg, 0.22 mmol). The mixture was stirred at room temperature for 10 min and then poured into 2 N HCl. The mixture was extracted with DCM (30 mL) and the organic layer was washed with aqueous NaHCO3, brine, dried over anhydrous sodium sulfate. After filtration and concentration, the crude product was purified by preparative HPLC to afford 5.5 mg of desired product. MS (ESI): 369 (MH+); 1H NMR (300 MHz, CDCl3) δ 9.09-9.06 (d, J=7.38 Hz, 1H), 8.22 (s, 1H), 7.60-7.58 (d, J=6.57 Hz, 1H), 7.06 (t, J=5.4 Hz, 1H), 3.01-2.93 (m, 4H), 2.44 (s, 3H), 1.92-1.80 (m, 4H), 1.49 (broad, 4H). mGluR5 PAM EC50: +++++. Fold shift at 10 μM: +.

Provenance & Evidence