4-Methoxybenzylamine → HCID 68328342, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-chloro-5-(1H-indol-5-yl)-1,2,4-thiadiazole (0.67 g, 2.85 mmol) and 4-methoxybenzylamine (1.95 g, 14.25 mmol, Aldrich) in DMSO (7 mL) was stirred for 12 h at 110° C. The reaction was cooled to RT and quenched with ice cold water (50 mL) and extracted into EtOAc (20 mL). The aqueous layer was back extracted with EtOAc (20 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by using silica-gel column chromatography (eluent: 30-40% EtOAc and petroleum ether) to give 5-(1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine (670 mg, 70.5%) as a off brown solid. MS (ESI, pos. ion) m/z: 337.1 (M+1); 1H-NMR (300 MHz, CDCl3): δ 8.44 (brs, 1H), 8.21 (d, J=9 Hz, 1H), 7.73 (dd, J=8.4, 1.8 Hz, 1H), 7.45 (d, J=8.4 Hz, 1H), 7.35 (d, J=8.7 Hz, 2H), 7.28-7.26 (m, 1H), 6.90 (dd, J=6.9, 2.1 Hz, 2H), 6.64 (m, 1H), 5.42 (m, 1H), 4.62 (d, J=7.6 Hz, 1H), 3.80 (s, 3H).

Provenance & Evidence