Methanol → HCID 59291672, compound

Participants

Reaction Steps

4-(6-(3-(1-Acetylpiperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)-5-(2-chlorophenylthio)pyridin-3-yloxy)benzaldehyde (30 mg, 0.0530 mmol) was dissolved in 1:1 EtOAc:methanol (2 mL) and NaBH4 (10.0 mg, 0.265 mmol) was added. After stirring 30 minutes the reaction was poured into aqueous NH4Cl, extracted with EtOAc and purified on silica gel (0 to 10% methanol in EtOAc) to afford 1-(4-(5-(3-(2-chlorophenylthio)-5-(4-(hydroxymethyl)phenoxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone (19.9 mg, 0.0350 mmol, 66.1% yield) as a white solid. 1H NMR (CDCl3) δ 9.23 (s, 1H), 8.30 (d, 1H), 7.64 (d, 1H), 7.43 (m, 1H), 7.38 (d, 2H), 7.16 (m, 2H), 7.01 (d, 2H), 6.76 (dd, 1H), 4.69 (d, 2H), 4.57 (d, 1H), 3.88 (d, 1H), 3.20 (t, 1H), 3.03 (m, 1H), 2.80 (t, 1H), 2.11 (s, 3H), 2.07 (m, 2H), 1.92-1.71 (m, 3H).

Provenance & Evidence