Quinoline → HCID 86749395, compound

Participants

Reaction Steps

A solution of (R)-N-{3-[5-(4-fluorophenylmethyl)thien-2-yl]-1-methyl-2-propynyl}-N-hydroxyurea (0.50 g, 1.57 mmol), prepared as in step 4, quinoline (0.25 mL, 2.11 mmol), and 5% palladium on calcium chloride poisoned with lead (0.025 g) in acetone (15 mL) was allowed to stir under hydrogen (atmospheric pressure) for 24 hours. The solution was filtered through celite and solvents removed in vacuo. The resulting oil was taken up in ethyl acetate (50mL) and washed with aqueous 1M H3PO4 (3×25 mL) and aqueous NaHCO3 (3×25 mL). The solution was dried (MgSO4) after which the solvent was evaporated to yield a yellow oil. The residue was purified by chromatography on silica gel (50% ethyl acetate/hexane/1% acetic acid). The resulting solid was crystallized from hot ethyl acetate/hexane to yield 0.145g (29%) of Z-N-[3-(5-(4-Fluorophenylmethyl)-thien-2-yl)-1-[R]-methyl-2-propenyl]-N-hydroxyurea. m.p. 123°-4° C., MS. (DCI/NH3) m/e 321 (M+H)+, 338 (M+NH4)+. 1H NMR (DMSO-d6, 300 MHz) δ1.16 (d,J=6.3 Hz, 3H), 4.1 (s, 2H), 5.25 (m, 1H), 5.67 (rid, J=9.0, 11.7 Hz, 1H), 6.35 (s, 2H), 6.43 (d, J=11.7 Hz, 1H), 6.83 (d, J=3.6 Hz, 1H), 6.94 (d, J=3.6 Hz, 1H), 7.13 (m, 2H), 7.32 (m, 2H), 9.18 (s, 1H). Anal calcd for C17H17FN2O2S: C, 59.98; H, 5.35; N, 8.74. Found C, 59.79; H, 5.25; N, 8.71.

Provenance & Evidence