Diisopropylethylamine → 5-{5-[4-[(1-Methylethyl)oxy]-3-(methyloxy)phenyl]-1,2,4-oxadiazol-3-yl}isoquinoline

Participants

Reaction Steps

A mixture of 4-[(1-methylethyl)oxy]-3-(methyloxy)benzoic acid (Journal of the American Chemical Society (1955), 77 757-8; 135 mg, 0.641 mmol), HATU (244 mg, 0.641 mmol), Hunig's base (0.3 ml, 1.718 mmol) in N,N-dimethylformamide (DMF) (1 ml) was stirred at room temperature for 1 hr before the addition of N-hydroxy-5-isoquinolinecarboximidamide (D1; 100 mg, 0.534 mmol) in N,N-dimethylformamide (DMF) (1 ml). The reaction mixture was stirred at room temperature for 2-3 hrs and then heated in a microwave at 140° C. for 1.5 hr. The reaction mixture was concentrated in vacuo, dissolved in 1-2 ml of N-methylpyrrolidinone and purified by Preparative HPLC (Waters Sunfire C18 column, eluting with solvents A/B (A: Water+0.1% Formic acid, B: MeCN+0.1% Formic acid)). The solvent was evaporated in vacuo to give the title compound (5 mg).

Provenance & Evidence