Hydrochloric Acid → HCID 86639687, compound

Participants

Reaction Conditions

Reaction Steps

A 10 mL round-bottomed flask was charged with 3-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)propanoic acid (60 mg, 0.16 mmol), triethylamine (0.091 ml, 0.65 mmol), and THF (3 mL). The reaction was cooled to 0° C., ethyl carbonochloridate (0.017 ml, 0.17 mmol) was added, and the reaction was stirred at 0° C. for 20 minutes. 1-Methylpiperazine (0.036 ml, 0.32 mmol) was added and stirred at 0° C. for 1.5 hours. The reaction was partitioned between EtOAc and water. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified on a silica gel column (15% methanol in EtOAc with NH4OH) to afford the title compound (59.8 mg, 70.2% yield) as a white solid after HCl salt formation. 1H NMR (DMSO-d6) δ 11.25 (bs, 1H), 11.05 (bs, 1H), 7.89 (s, 1H), 7.62 (m, 3H), 7.45-7.33 (m, 3H), 6.83 (s, 1H), 5.32 (s, 2H), 4.43 (d, 1H), 4.06 (d, 1H), 3.47 (t, 1H), 3.38 (d, 2H), 3.01 (m, 2H), 2.84 (m, 3H), 2.74 (m, 5H), 2.32 (s, 3H). Mass spectrum (apci) m/z=452.2 (M+H-2HCl).

Provenance & Evidence