Hydrochloric Acid → (R)-N-hydroxy-4-(2-methyl-1-(4-(3-phenylisoxazol-5-yl)thiazol-2-ylamino)propyl)benzamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-((R)-2-methyl-1-thioureidopropyl)-N-(tetrahydro-2H-pyran-2-yloxy)benzamide (0.0252 g, 0.0717 mmol) and 5-(bromoacetyl)-3-phenylisoxazole (0.0191 g, 0.0717 mmol) in 1,4-dioxane (0.50 mL) was heated at 40° C. for 1 h. The solution was diluted with DCM (0.50 mL) and hydrochloric acid (0.20 mL, 0.80 mmol, 4.00 M of in 1,4-dioxane) was added. The reaction was stirred at rt for 3 h. The mixture was evaporated to dryness, the residue dissolved in DMSO and the solution purified on prep-HPLC to give (R)—N-hydroxy-4-(2-methyl-1-(4-(3-phenylisoxazol-5-yl)thiazol-2-ylamino)propyl)benzamide as a white solid (0.0173 g, 56%). LC-MS: (FA) ES+ 435. 1H NMR (dmso-d6, 400 MHz) δ11.13 (s, 1H), 9.00 (s, 1H), 8.52 (d, J=8.6 Hz, 1H), 7.90 (m, 2H), 7.70 (d, J=8.3 Hz, 2H), 7.51 (dd, J=5.1, 1.9 Hz, 3H), 7.44 (d, J=8.3 Hz, 2H), 7.26 (s, 1H), 7.09 (s, 1H), 4.48 (t, J=8.1 Hz, 1H), 2.10 (m, 1H), 1.00 (d, J=6.6 Hz, 3H), 0.78 (d, J=6.7 Hz, 3H).

Provenance & Evidence