Hydrochloric Acid → HCID 25099654, compound

Participants

Reaction Steps

A 250 mL flask was charged with 3-phenoxy-N-(3-(piperidin-4-yl)-1,2,4-thiadiazol-5-yl)-5-(thieno[3,2-b]pyridin-7-ylthio)pyridin-2-amine trihydrochloride (5.6 g, 8.92 mmol), triethylamine (9.94 mL, 71.3 mmol), and CH2Cl2 (100 mL). Acetic anhydride (1.26 mL, 13.4 mmol) was added and the reaction was stirred at ambient temperature for 10 minutes. The reaction was poured into saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica (5 to 10% methanol in EtOAc) to afford 1-(4-(5-(3-phenoxy-5-(thieno[3,2-b]pyridin-7-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone dihydrochloride (4.16 g, 73.6% yield) as a yellow solid after HCl salt formation. 1H NMR (d6-DMSO) δ 12.48 (bs, 1H), 8.56 (d, 1H), 8.53 (d, 1H), 8.28 (d, 1H), 7.65 (d, 1H), 7.57 (d, 1H), 7.40 (m, 2H), 7.18 (m, 1H), 7.14 (m, 2H), 7.07 (d, 1H), 4.32 (m, 1H), 3.20 (m, 1H), 3.07 (m, 1H), 2.77 (m, 1H), 2.01 (m, 5H), 1.73 (m, 1H), 1.59 (m, 1H). Mass spectrum (apci) m/z=561.3 (M+H-2HCl).

Provenance & Evidence