Sodium Bicarbonate → 3-[[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-ylmethyl]-(3-fluoro-benzyl)-amino]-propionamide

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Reaction Steps

To a mixture of 3-(3-Fluoro-benzylamino)-propionamide (98 mg, 0.5 mmol), 1-(3,5-dichloro-benzyl)-1H-imidazole-2-carbaldehyde, (see Example 2) (102 mg, 0.4 mmol) and CH2Cl2 (2 mL) was added NaBH(OAc)3 (119 mg, 0.56 mmol). The mixture was stirred at ambient temperature for 3 h before addition of saturated NaHCO3 (8 mL). The mixture was extracted with CH2Cl2 (2×15 mL) and the combined CH2Cl2 extracts dried over Na2SO4. Volatiles were removed in vacuo and the residue purified by column chromatography (silica gel, 20:1 CH2Cl2/MeOH) to provide the title compound (71 mg, 40%) as colorless, viscous oil: ESI MS m/z 435 [C21H21Cl2FN4O+H]+.

Provenance & Evidence