2-[6-(methylamino)pyridin-3-yl]-1,3-benzothiazol-6-ol → 5-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

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Reaction Steps

5-(6-Methoxy-1,3-benzothiazol-2-yl)pyridin-2-amine (190 mg, 0.74 mmol) was exposed to the procedure used for the preparation of 2-[6-(methylamino)pyridin-3-yl]-1,3-benzothiazol-6-ol. After neutralization, the precipitate was filtered off and washed with water. The crude solid was slurred in hot EtOAc/MeOH 95:5 and filtered. The filtrate was concentrated under reduced pressure and the residue was subjected to flash chromatography (EtOAc/MeOH 95:5) to give a product that was chromatographed once more (DCM/MeOH 95:5) to yield the title compound (65 mg). 1H NMR δ 9.74 (s, 1H) 8.53 (d, 1H) 7.93 (dd, 1H) 7.73 (d, 1H) 7.35 (d, 1H) 6.93 (dd, 1H) 6.61 (br s, 2H) 6.55 (d, 1H); MS m/z (M+H) 244.

Provenance & Evidence