Triethylamine → Methyl 3-(2-(3-(benzyloxy)pyridin-2-ylamino)thiazol-4-yl)propanoate

Participants

Reaction Steps

1-(3-(Benzyloxy)pyridin-2-yl)thiourea (3.30 g, 12.7 mmol), methyl 5-bromo-4-oxopentanoate (3.19 g, 15.3 mmol) (prepared according to Synthetic Communications (1994) 2557-2562), and triethylamine (3.10 mL, 22.3 mmol) were heated in methanol (100 mL) at reflux for 3 hours according to the method of Example 2, Step C, to provide methyl 3-(2-(3-(benzyloxy)pyridin-2-ylamino)thiazol-4-yl)propanoate (3.82 g, 81.3% yield) as a light yellow powder: 1H NMR (DMSO-d6) δ 9.93 (bs, 1H), 7.86 (d, 1H), 7.57 (d, 2H), 7.34-7.42 (m, 4H), 6.89 (m, 1H), 6.63 (s, 1H), 5.26 (s, 2H), 3.60 (s, 3H), 2.85 (t, 2H), 2.69 (t, 2H). Mass spectrum (esi) m/z=370 (100).

Provenance & Evidence