Phosphorus oxychloride → HCID 59225701, compound

Participants

Reaction Conditions

Reaction Steps

The crude N′-acetyl-3-(2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazol-4-yl)propanehydrazide (0.339 g, 0.691 mmol) was added acetonitrile (25 mL), POCl3 (0.380 ml, 4.15 mmol) and the mixture heated at 50° C. overnight. Additional POCl3 (0.5 mL) was added and the reaction was stirred for 3 days 50° C. Additional 0.5 ml POCl3 (0.5 mL) was added and the reaction was stirred at 50° C. for an additional 18 hours. The reaction was then concentrated to dryness, diluted with water, extracted with DCM, dried over Na2SO4, filtered, concentrated to a residue and purified by prep HPLC and then on a silica gel column, eluting with 75% EtOAc/Hexanes, to give 3-(benzyloxy)-5-bromo-N-(4-(2-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl)thiazol-2-yl)pyridin-2-amine (0.092 g, 28% yield) as a white solid. 1H NMR (DMSO-d6) δ 2.44 (s, 3H), 3.01 (t, J=7.6 Hz, 2H), 3.17 (t, J=7.6 Hz, 2H), 5.29 (s, 2H), 6.73 (s, 1H), 7.35 (t, J=7.2 Hz, 1H), 7.42 (t, J=7.2 Hz, 2H), 7.59 (d, J=7.2 Hz, 2H), 7.63 (d, J=1.6 Hz, 1H), 7.97 (d, J=1.8 Hz, 1H), 10.31 (s, 1H); Mass Spectrum (apci) 472 (M+H).

Provenance & Evidence