Hydrochloric Acid → HCID 178461689, compound

Participants

Reaction Steps

A solution of iodine (135 mg, 0.53 mmol) in EtOH (5 ml) was added dropwise to a cooled mixture (0-5° C.) of the intermediate 12b (150 mg, 0.40 mmol) and K2CO3 (212 mg, 1.53 mmol) in EtOH (5 ml). The reaction mixture was stirred for 24 h at room temperature. Water (10 ml) was added and pH adjusted to 3 by 1M HCl. The aqueous layer was extracted with EtOAc (3×10 ml); the collected organic extracts were dried over anhydrous Na2SO4 and, after solvent evaporation, the purification of the crude by flash chromatography (CH2Cl2/CH3OH 95:5) afforded 5-[(1R)-1-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)ethyl]isothiazol-3-ol (12) (82 mg, 0.22 mmol) as a white solid (41%). [α]D=−31 (c=1; CH3OH); 1H-NMR (CDCl3): δ 10.60 (bs, 1H, OH), 9.15 (bs, 1H, NH), 7.40 (d, 2H, J=7 Hz), 7.25 (d, 2H, J=7 Hz), 7.00 (s, 1H), 5.50 (s, 1H), 3.80 (q, 1H, J=7 Hz), 1.55 (d, 3H, J=7 Hz).

Provenance & Evidence