Propanal → (S)-10-[3-(2-Methoxy-ethyl)-4-propyl-piperazin-1-yl]-2-trifluoromethyl-4H-3-thia-1,4,9-triaza-benzo[f]azulene

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Reaction Steps

Add sodium triacetoxyborohydride (0.273 g, 1.29 mmol), and then propionaldehyde (0.083 mL, 1.15 mmol) to (S)-10-[3-(2-methoxy-ethyl)-piperazin-1-yl]-2-trifluoromethyl-4H-3-thia-1,4,9-triaza-benzo[f]azulene (0.353 g, 0.858 mmol) in anhydrous dichloroethane (15 mL) and stir at ambient temperature overnight. Add saturated aqueous sodium bicarbonate and extract aqueous phase with dichloromethane. Wash organics with saturated aqueous sodium chloride, and dry (sodium sulfate), filter, and concentrate under reduced pressure to a residue (0.29 g). Purify the residue by flash chromatography, eluting with a gradient of a 3% solution of 2M ammonia in methanol, in dichloromethane, (0-100%) to give the title compound (0.287 g, 74%): mass spectrum (APCI, m/e): 454 (M+1); NMR (1H, 300 MHz, DMSO-d6): δ 8.46 (s, 1H), 6.96-6.82 (m, 3H), 6.71 (m, 1H), 3.46 (br. m, 3H), 3.31-3.17 (m, 3H), 3.15 (s, 3H), 2.73 (m, 1H), 2.58-2.44 (m, 2H), 2.31 (m, 2H), 1.67 (m, 2H), 1.40 (m, 2H), 0.83 (t, 3H, J=7.5 Hz).

Provenance & Evidence