Isopropanol → 5-(3-(4-isopropoxypyrimidin-2-yl)-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with IPA (1 mL, 13.06 mmol) and 5-(3-(4-chloropyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (80 mg, 0.157 mmol), followed by the addition of 60% of NaH in mineral oil (15.72 mg, 0.393 mmol, Aldrich). The reaction was stirred and heated in a Initiator microwave reactor at 100° C. for 30 min, then the solvent was removed. The residue was purified with RP-HPLC (eluent: 10-50% MeCN in water with 0.1% TFA). The fractions containing the product were combined and concentrated to remove AcCN. The remaining mixture was neutralized with NH4OH and filtered and dried to give 5-(3-(4-isopropoxypyrimidin-2-yl)-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (6.0 mg, 0.016 mmol, 10.09%) as an off-white solid. MS (ESI, pos. ion) m/z: 379.1 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 11.99 (1H, br. s.), 9.00 (1H, s), 8.50 (1H, d, J=5.7 Hz), 8.30 (1H, s), 7.52-7.72 (3H, m), 6.60 (1H, d, J=5.9 Hz), 5.47-5.62 (1H, m), 3.67-3.81 (1H, m), 1.42 (6H, d, J=6.1 Hz), 1.23 (6H, d, J=6.5 Hz).

Provenance & Evidence