2-Amino-N-isopropylacetamide → HCID 44203076, compound

Participants

Reaction Steps

To a solution of 5-fluoro-2-nitrobenzoic acid (370 mg, 2.0 mmol) in anhydrous DMF (5 mL) was added 1-hydroxybenzotriazole hydrate (330 mg, 2.4 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (460 mg, 2.4 mmol) and 2-amino-N-isopropylacetamide (INTERMEDIATE I.1) (230 mg, 2.0 mmol). The resultant mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated in vacuo, the crude yellow residue dissolved in EtOAc (20 mL) and washed with dilute HCl (aq.) (3×5 mL), sat. NaHCO3 (aq.) (3×5 mL) and brine (1×5 mL). The organic layer was dried (Na2SO4), concentrated in vacuo and purified by chromatography on silica gel with MeOH:DCM (1:19, v/v) as eluent to afford 5-fluoro-N-(isopropylcarbamoylmethyl)-2-nitrobenzamide (INTERMEDIATE IV.1) (400 mg, 1.4 mmol, 70%) as yellow solid.

Provenance & Evidence