Hydrochloric Acid → HCID 58689910, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-nitro-benzoic acid N′-isopropyl-hydrazide (84 mg, 0.378 mmol), (5-fluoro-2′-trifluoromethoxy-biphenyl-2-yloxy)-acetic acid (100 mg, 0.302 mmol), and DIPEA (0.329 ml, 1.89 mmol) in DMF (5 ml) was treated with PyBroP (176 mg, 0.378 mmol) and let stir at 25° C. overnight. The reaction mixture was diluted with 70 ml ethyl acetate and extracted with 1N HCl (2×30 ml), saturated sodium bicarbonate (2×30 ml). The organic layer was dried over sodium sulfate, filtered, and concentrated to a gum (150 mg). The crude material (75 mg, 0.14 mmol) dissolved in EtOH (5 ml) containing acetic acid (2 drops), concentrated HCl (20 μl), isobutyraldehyde (152 μl, 1.68 mmol) and 10% palladium on carbon (10 mg) This mixture was hydrogenated at 20 psi at rt for 5 hours. The reaction mixture was filtered through celite diluted with ethyl acetate, washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered and concentrated. The crude product was triturated with 1% ethyl acetate/hexanes to give an off-white solid (31 mg, 39%). MS m/e 562 (M+H+)

Provenance & Evidence