3,5-Dichlorobenzoic acid → HCID 68981086, compound

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Reaction Steps

[(2S)-2-(3,4-Dichlorophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]methylamine hydrochloride (see Method 1; 89 mg, 0.21 mmol) was dissolved in DMF (2 mL) and to the resultant solution were added 3,5-dichlorobenzoic acid (44 mg, 0.23 mmol), TBTU (80 mg, 0.25 mmol) and DIPEA (108 mg, 0.84 mmol) in the given order. The solution was stirred at room temperature for 1.5 h, diluted with water and then neutralized by the addition of NaHCO3. The mixture was extracted twice with ethyl acetate and the combined organic solutions were dried over MgSO4. The solvent was removed by evaporation to yield 79 mg of crude product. The product was purified by reversed phase chromatography using a mixture of acetonitrile and 0.1 M ammonium acetate aq. There was obtained 43 mg (37%) of the title compound as a white solid. 1 H NMR (500 MHz, CD3CN): 1.3-1.8 (cm, 3H), 2.0-4.6 (cm, 23H), 6.8-7.7 (cm, 5H), 8.0 (d, 1H); LCMS: m/z 560 (M+1)+.

Provenance & Evidence