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

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Reaction Steps

Combine (S)-10-[3-(2-methoxy-ethyl)-4-methyl-piperazin-1-yl]-4H-3-thia-1,4,9-triaza-benzo[f]azulene-2-carboxylic acid ethyl ester (0.49 g, 1.18 mmol) in 5.0 mL THF, add 2.95 mL of LiAlH4 (1.0 M THF) dropwise at ice-water bath. After addition, remove the ice bath, stir the reaction mixture at RT. After half hour, quench the reaction by adding 1.0 N NaOH cautiously until no gas evolves. Pass the suspension through celite plug, wash repeatedly with ether, and concentrate the organic solution to a residue. Purify by flash chromatography affords 0.22 g of the title compound: mass spectrum (electrospray) (m/e): 374.0 (M+1), 372.1 (M−1); 1H NMR (400 MHz, DMSO-d6): 7.79 (s, 1H), 6.86-6.75 (m, 3H), 6.69-6.66 (m, 1H), 5.89 (br, 1H), 4.50 (d, 2H, J=4.4 Hz), 4.04-3.93 (m, 2H), 3.38-3.33 (m, 2H), 3.30 (s, 3H), 2.84-2.60 (m, 4H), 2.46-2.41 (m, 1H), 1.49 (q, 2H, J=6.6 Hz).

Provenance & Evidence