Hydrochloric Acid → HCID 71480921, compound

Participants

Reaction Steps

To a solution of N-(2-chloro-5-(diphenylmethyleneamino)pyridin-3-yl)cyclopropanesulfonamide (0.300 g, 0.728 mmol) in THF (5 mL) was added hydrochloric acid, In (1.092 mL, 1.092 mmol). The reaction was stirred at rt in closed system. After 30 min, LC/MS showed no sign of starting materials with desired product mass as the major peak. The reaction mixture was partitioned between EtOAc and sat. NaHCO3. The aqueous layer was extracted with more EtOAc (2×10 mL). The combined organic layer were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (40 g, 3% MeOH in DCM) to afford the desired product as a yellow solid (170 mg). MS (ESI pos. ion) m/z: 248.0. 1H NMR (300 MHz, CDCL3) δ ppm 1.04 (d, J=6.58 Hz, 2H) 1.13-1.32 (m, 2H) 2.51 (t, J=4.60 Hz, 1H) 3.85 (br. s., 2H) 6.63 (br. s., 1H) 7.35 (s, 1H) 7.68 (s, 1H).

Provenance & Evidence