Cesium carbonate → 2-((1S)-1-((5-amino-1,3,4-thiadiazol-2-yl)amino)ethyl)-1-cyclopropyl-N-methyl-1H-benzimidazole-7-carboxamide

Participants

Reaction Steps

A mixture of (S)-2-(1-aminoethyl)-1-cyclopropyl-N-methyl-1H-benzo[d]imidazole-7-carboxamide (prepared in example 20) (63.5 mg, 0.25 mmol), cesium carbonate (80 mg, 0.25 mmol) and 2-amino-5-bromo-[1,3,4]thiadiazole (44.3 mg, 0.25 mmol) in EtOH (5 mL) under N2 was stirred at rt for 18 h. The reaction mixture was concentrated in vacuo. The residue was diluted with EtOAc, washed with water, brine, dried over magnesium sulfate, and concentrated in vacuo. Purification of the residue by flash chromatography over silica gel, using 0 to 10% gradient of MeOH in DCM with 0.2% NH4OH as eluent to give 2-((1S)-1-((5-amino-1,3,4-thiadiazol-2-yl)amino)ethyl)-1-cyclopropyl-N-methyl-1H-benzimidazole-7-carboxamide: 1H NMR (400 MHz, DMSO-d6) δ 8.46-8.39 (1H, m); 7.62 (1H, d, J=8.0 Hz), 7.44 (1H, d, J=8.0 Hz), 7.24-7.16 (2H, m); 6.22 (2H, s), 5.46-5.37 (1H, m), 3.40-3.30 (1H, m), 2.82 (3H, d, J=4.0 Hz), 1.55 (3H, d, J=4.0 Hz), 1.22-1.15 (1H, m), 1.12-1.04 (1H, m), 1.01-0.92 (1H, m), 0.83-0.74 (1H, m); LC-MS (ESI) m/z 358.0 [M+H]+.

Provenance & Evidence