Acetic Acid → 5-(4-{4-[(2S)-2-Hydroxy-3-(pyridin-3-yloxy)-propylamino]-piperidin-1-yl}-benzyl)-thiazolidine-2,4-dione

Participants

Reaction Steps

(2S)-1-Amino-3-(3-pyridinyloxy)-2-propanol (0.21 g, 1.25 mmol) (which was obtained in Example 124) and 5-[4-(4-oxo-1-piperidineyl)benzyl]-1,3-thiazolidine-2,4-dione (which was obtained in Example 38) (0.413, 1.25 mmol) were mixed in N,N-dimethylformamide (12 mL) and then treated with sodium triacetoxyborohydride (0.56 g, 2.5 mmol) and acetic acid (0.26 mL). After stirring at room temperature under a nitrogen atmosphere for one day, the mixture was purified by column chromatography (dichloromethane/methyl alcohol 85/5) to give the title compound as a yellow solid (0.25 g, 56% yield); mp: 130-132° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.20-1.54 (m, 2H), 1.90-2.02 (m, 2H), 2.67 (t, 2H), 2.78-2.97 (m, 4H), 3.22-3.26 (m, 1 H), 3.35 (brs, 2H), 3.64-3.70 (d, 2H), 3.97-4.08 (m, 3H), 4.60-4.63 (m, 1H), 6.84-6.86 (m, 2 H), 7.03-7.05 (m, 2H), 730-7.36 (m, 1H), 7.38-7.40 (m, 1H), 8.16-8.17 (m, 1H), 8.8.29-8.30 (m, 1H); MS (ES) m/z: 457 (MH+).

Provenance & Evidence