Hydrochloric Acid → HCID 67308696, compound

Participants

Reaction Conditions

Reaction Steps

Add 5-(6-methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-yl)thiophene-2-carboxamide (79 mg, 0.16 mmol) and phosphoryl chloride (13 mL, 139.9 mmol) to a round bottom flask under nitrogen. Warm the resulting mixture to 100° C. and stir for 15 min. Cool the mixture to room temperature and concentrate in vacuo to give a yellow residue. Carefully quench the resulting residue with methanol and load onto an SCX acidic ion exchange column. Flush the column with methanol then elute desired material with 2M ammonia in methanol. Concentrate the ammonia containing eluent in vacuo to give a pale yellow solid. Dissolve the resulting solid in dichloromethane and treat with HCl (1M in ether, 5 mL). Concentrate in vacuo to obtain the title compound (81.5 mg, 0.16 mmol) 1H NMR (d6-DMSO) δ 0.82-0.73 (m, 1H), 1.33-1.23 (m, 4H), 2.88-2.80 (m, 2H), 3.36-3.31 (m, 5H), 3.81 (s, 3H), 4.23-4.19 (m, 2H), 6.73-6.63 (m, 2H), 6.87-6.77 (m, 2H), 7.15-7.09 (m, 1H), 7.41-7.36 (m, 1H), 7.62-7.54 (m, 1H), 7.87-7.77 (m, 3H), 8.09-8.05 (m, 1H), 10.58-10.45 (m, 1H).

Provenance & Evidence