Isopropylamine → N-isopropyl-5-(3-(2-(isopropylamino)pyrimidin-4-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 5-(3-(2-chloropyrimidin-4-yl)-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (100 mg, 0.196 mmol) and isopropylamine (16.88 μl, 0.196 mmol) in NMP (2.0 mL). The reaction mixture was stirred and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 135° C. for 1 h. aq. NaOH (0.5 mL, 5 M) was added to the mixture and the reaction was heated in the microwave at 100° C. for 20 min. The mixture was purified with preparative HPLC (eluting with 10-50% MeCN in water with 0.1% TFA in each solvent) and the fractions containing the product were combined and concentrated in vacuo to remove MeCN. The resulting mixture was extracted with CHCl3/iPrOH (4:1) and the combined organic layers were dried (MgSO4), filtered and concentrated to give N-isopropyl-5-(3-(2-(isopropylamino)pyrimidin-4-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (29 mg, 0.077 mmol, 39.1% yield) as a yellow solid. MS (ESI, pos. ion) m/z: 378.0 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 11.95 (1H, s), 8.99 (1H, br. s.), 8.30 (1H, s), 8.17 (1H, d, J=5.1 Hz), 7.64 (1H, dd, J=8.5, 1.5 Hz), 7.57 (1H, d, J=8.6 Hz), 7.45 (1H, d, J=7.2 Hz), 7.00 (1H, d, J=5.3 Hz), 6.70 (1H, br. s.), 4.17-4.29 (1H, m), 3.71-3.83 (1H, m), 1.20-1.30 (12H, m).

Provenance & Evidence