Benzoic acid, 3,5-dibromo- → HCID 68977965, compound

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Reaction Steps

[(2S)-2-(Fluorophenyl)-4-(3-morpholin-4-ylazetidin-1-yl)butyl]methylamine dihydrochloride (see Method 4; 292 mg, 0.68 mmol), 3,5-dibromobenzoic acid (215 mg, 0.77 mmol) and DIPEA (350 mg, 2.71 mmol) were dissolved in DMF (20 mL) and to the resultant solution was added TBTU (250 mg, 0.78 mmol) at 0° C. The mixture was stirred at RT for 2 h and then the solvent was removed by evaporation. The residue was diluted with ethyl acetate and then washed thrice with an aqueous solution of NaHCO3. The organic solution was combined with another preparation of the title compound (as free base) being prepared by a similar method (68 mg). The combined organic solutions were then dried over MgSO4 and the solvent was removed by evaporation to yield 344 mg. The product was purified by reversed phase chromatography using a mixture of acetonitrile and 0.1 M ammonium acetate aq. The collected fractions were freeze-dried and the residue was then dissolved in a mixture of water and acetonitrile. The solution was acidified with hydrochloric acid (2 M) and again freeze-dried. There was obtained 267 mg (55%) of the title compound as a grey solid. 1H NMR (500 MHz, CD3OD): 1.8-2.1 (cm, 2H), 2.7-4.8 (cm, 21H), 6.9-7.8 (cm, 7H); LCMS: m/z 584 (M+1)+.

Provenance & Evidence