Hydrochloric Acid → HCID 86639693, compound

Participants

Reaction Steps

A 1 dram vial was charged with methyl 3-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)propanoate (70 mg, 0.168 mmol) and DMSO (2 mL). Potassium 2-methylpropan-2-olate (56.7 mg, 0.505 mmol) was added and the reaction was stirred for 5 minutes. 2-Chloro-4-nitropyridine (53.4 mg, 0.337 mmol) was added and the reaction was stirred for 10 minutes. The reaction was poured into saturated aqueous NH4Cl and extracted with EtOAc. The organic phase was washed with water. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified on a silica gel column (20% EtOAc/hexanes) to afford the title compound (45.7 mg, 52.8% yield) as a white solid after HCl salt formation. 1H NMR (DMSO-d6) δ 10.92, (bs, 1H), 8.15 (m, 2H), 7.69 (d, 1H), 7.56 (m, 2H), 7.43-7.32 (m, 3H), 7.10 (d, 1H), 6.97 (dd, 1H), 6.80 (s, 1H), 5.34 (s, 2H), 2.30 (s, 3H). Mass spectrum (apci) m/z=441.0 (M+H-2HCl).

Provenance & Evidence