Sodium Acetate → HCID 21899130, compound

Participants

Reaction Steps

and (e) To a suspension of 409 mg N-(5-Formyl-1-phenyl-1H-benzoimidazol-2-yl)-3-trifluoromethylbenzamide (1.00 mmol, 1.00 equiv) prepared above in Example 7 in 40 mL of 1:9 HOAc:MeOH, 0.205 g NaOAc (2.50 mmol, 2.50 equiv), and 0.84 g ethyl 4-aminobutyrate hydrochloride (5.00 mmol, 5.00 equiv) was added 0.138 g NaCNBH3 (2.00 mmol, 2.00 equiv). The pink suspension was allowed to stir 20 h, after which time the resulting brown solution was diluted with 50 mL sat. NaHCO3 and 50 mL EtOAc. The aqueous layer was extracted (2×EtOAc) and the combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. Purification by flash chromatography (SiO2, 1-2% MeOH/CH2Cl2 with 1% aq. NH4OH) gave 300 mg of the product as a colorless solid (0.57 mmol). A solution of 105 mg of this product (0.20 mmol, 1.00 equiv) in 20 mL toluene and 2 mL HOAc was heated to reflux temperature for 1 h. The solution was concentrated under reduced pressure and purified by flash chromatography (SiO2, 2-5% MeOH/CH2Cl2 with 1% aq. NH4OH) to give 80 mg of the product as a colorless solid (0.17 mmol). 1H NMR (CDCl3, 400 MHz) δ 13.03 (s, 1H), 8.31 (s, 1H), 8.28 (d, J=7.8 Hz, 1H), 7.85 (d, J=7.7 Hz, 1H), 7.65-7.75 (m, 5H), 8.26 (t, J=7.1 Hz, 1H), 7.53 (s, 1H), 7.16 (m, 2H), 4.47 (s, 2H), 3.26 (t, J=7.0 Hz, 2H), 2.31 (t, J=8.0 Hz, 2H), 1.94 (m, 2H).

Provenance & Evidence