Ethanolamine → HCID 58367154, compound

Participants

Reaction Steps

Prepared using General Procedure 20: To a stirred solution of 5-(5-(1-hydroxy-2,3-dihydro-1H-inden-4-yl)thiazol-2-yl)-2-isopropoxybenzonitrile (20 mg, 0.05 mmol) in DCM (1 mL) was added thionyl chloride (12.6 mg, 0.106 mmol) at 0° C. The reaction was stirred at room temperature for 3 h. The solvent was evaporated and the crude chloride re-dissolved in dimethyl acetamide (1 mL). Diisopropyl ethylamine (20.5 mg, 0.16 mmol) and ethanolamine (9.7 mg, 0.16 mmol) were added and the reaction mixture was stirred at 70° C. overnight. The reaction mixture was quenched with water (200 uL) and purified by preparative HPLC to afford 11 mg (46%) of 5-(5-(1-(3-hydroxyazetidin-1-yl)-2,3-dihydro-1H-inden-4-yl)thiazol-2-yl)-2-isopropoxybenzonitrile 208. LCMS-ESI (m/z) calculated for C25H25N3O2S: 431.1; found 432.1 [M+H]+, tR=6.48 min (Method 2).

Provenance & Evidence