Ammonia → HCID 68328565, compound

Participants

Reaction Conditions

Reaction Steps

A sealed tube was charged with tert-butyl 3-(6-(4-methylpiperazin-1-yl)pyridin-2-yl)-5-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)-1H-indole-1-carboxylate (300 mg, 0.541 mmol) followed by ammonia in DMSO (10 mL). The reaction was heated at 120° C. for 4 h. Ice/H2O and EtOAc were added to the mixture. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layer was dried, filtered and concentrated. The residue was purified with RP-HPLC to give 5-(3-(6-(4-methylpiperazin-1-yl)pyridin-2-yl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine (40 mg, 19%). MS (ESI, pos. ion) m/z: 392.1 (M+1); 1H-NMR (DMSO-d6, 300 MHz) δ 11.76 (1H, s), 10 (1H, brs), 8.8 (1H, s), 8.16 (1H, s), 7.5-7.67 (4H, m), 7.28-7.3 (1H, d), 6.75-6.79 (1H, d), 4.54-4.57 (2H, d), 3.6-3.65 (2H, d), 3.17-3.24 (4H, m), 2.91 (3H, s).

Provenance & Evidence