Cysteamine Hydrochloride → HCID 18416156, compound

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Reaction Steps

A solution of 6-bromo-7-chloro-2-isopropoxy-4-(trifluoromethyl)quinoline (0.500 g, 1.36 mmol), 2-aminoethanethiol hydrochloride (0.185 g, 1.63 mmol), NaH (60% in mineral oil, 0.136 g, 3.40 mmol) in 6.8 mL DMF was stirred at 0° C., then allowed to warm to rt. After 4 h, the mixture was poured into a cold saturated NH4Cl:water (60 mL, 1:1). The solution was extracted with EtOAc (2×60 mL), and the combined organic layers washed sequentially with water (30 mL), brine (30 mL), dried over MgSO4, filtered, and concentrated. Flash chromatography (9:1 CH2Cl2:MeOH) afforded 0.404 g (73%) of 2-{[6-bromo-2-isopropoxy-4-(trifluoromethyl)-7-quinolinyl]sulfanyl}-1-ethanamine, a yellow-brown solid. Data for 2-{[6-bromo-2-isopropoxy-4-(trifluoromethyl)-7-quinolinyl]sulfanyl}-1-ethanamine: 1H NMR (400 MHz, CDCl3) δ 8.13 (broad s, 1H), 7.63 (s, 1H), 7.10 (s, 1H), 5.54 (hept, 1H, J=6.2), 3.17-3.25 (m, 2H), 3.08-3.15 (m, 2H), 1.41 (d, 6H, J=6.2).

Provenance & Evidence