Hydrochloric Acid → HCID 86585414, compound

Participants

Reaction Steps

To 4-{[4-(2-butynyloxy)phenyl]sulfonyl}-N-hydroxy-4-piperidinecarboxamide hydrochloride (prepared from Example 76) (2.5 g, 6.43 mmol) and methyl 4-(bromomethyl)benzoate (1.62 g, 7.07 mmol) in methanol (100 mL) at 50° C. was added triethylamine (2.25 mL, 16.1 mmol). After 30 min additional methanol (50 mL) was added. After 18 h the reaction mixture was concentrated in vacuo and 1N aqueous hydrochloric acid (10 mL) and water was added. The resulting solid was isolated and to it was added methanol (20 mL) and 1N hydrochloric acid in diethylether (15 mL). To the resulting solution was added diethyl ether. Trituration of the precipitate gave methyl ({4-{[4-(2-butynyloxy)phenyl]sulfonyl}-4-[(hydroxyamino)carbonyl]-1-piperidinyl}methyl)benzoate hydrochloride as a white powder (2.4 g). 1H NMR (dmso d6, 300 MHz) δ1.85 (t, 3H, CH3, J=2.2 Hz), 2.1-3.5 (m, 8H, CH2), 3.87 (S, 3H, OCH3), 4.40 (bd s, 2H, NCH2Ar), 4.89 (q, 2H, OCH2, J=2.2 Hz), 7.1-8.1 (m, 8H, ArH), 9.3-11.2 (m, 3H, NH, NHOH). Electrospray MS m/z 501.5 (M+H)+

Provenance & Evidence