Triethylamine → Methyl 3-(2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazol-4-yl)propanoate

Participants

Reaction Steps

1-(3-(Benzyloxy)-5-bromopyrazin-2-yl)thiourea (2.00 g, 5.91 mmol), methyl 5-bromo-4-oxopentanoate (1.48 g, 7.10 mmol) (prepared according to Synthetic Communications (1994) 2557-2562), and triethylamine (1.44 mL, 10.3 mmol) were heated in methanol (50 mL) at reflux for 3 hours according to the method of Example 2, Step C, to provide methyl 3-(2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazol-4-yl)propanoate (1.51 g, 57%) as a white powder: 1H NMR (DMSO-d6) δ 11.16 (bs, 1H), 8.02 (s, 1H), 7.59 (d, 2H), 7.36-7.44 (m, 3H), 6.71 (bs, 1H), 5.43 (s, 2H), 3.59 (s, 3H), 2.85 (t, 2H), 2.69 (t, 2H). Mass spectrum (esi) m/z=449 (96), 451 (100).

Provenance & Evidence