Water → HCID 15980921, compound

Participants

Reaction Steps

To a mixture of (5-amino-pyridin-2-yloxy)-acetic acid methyl ester (40 mg, 0.19 mmol) and 4-azido-2-hydroxy-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester (50 mg, 0.192 mmol) in DCM (5 mL) was added DIPEA (66 μL, 0.38 mmol). The mixture was stirred for 15 h at an ambient temperature and was poured into water. The aqueous mixture was extracted with ethyl acetate (3×25 mL) and the combined extracts were washed with brine and dried over magnesium sulfate. Filtration and concentration gave a solid residue that was suspended in a small amount of ethyl acetate (3 mL) and was collected by filtration. This afforded 35.6 mg (54%) of (5-(4-azido-2-hydroxy-benzoylamino)-pyridin-2-yloxy)-acetic acid methyl ester: 1H NMR (300 MHz, acetone-d6) δ 11.78 (bs, 1H), 9.89 (s,1H), 7.90 (m, 1H), 7.54 (m, 2H), 6.51 (m, 1H), 6.27 (m, 1H), 6.20 (m, 1H), 4.44 (s, 2H) 3.19 (s, 3H); MS (EI) m/z 341.99 (M−H)−.

Provenance & Evidence