Sodium Carbonate → HCID 16678949, compound

Participants

Reaction Steps

(1H-Benzimidazol-1-yl)acetic acid (50 mg, 0.28 mmol) (Example 1B) suspended in dichloromethane (5 mL) and diisopropylethylamine (0.19 mL, 1.12 mmol) and stirred for 1 h at room temperature until a clear solution was observed. 3-m-Tolyl-isoxazol-5-yl amine (53 mg, 0.28 mmol) and bromotripyrrolidinophosphonium hexaflurophosphate (PyBroP) (130 mg, 0.28 mmol) were then added and stirred for 24 h at room temperature. Sodium carbonate was then added and the mixture passed through a hydrophobic frit. The organic layer was collected and evaporated to dryness. The residue was then purified by preparative HPLC affording title compound 1 mg. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.34 (3H, s), 5.07 (2H, s), 6.50 (1H, s), 7.17-7.24 (3H, m), 7.33 (1H, t, J=7.6 Hz), 7.52 (2H, t, J=8.6 Hz), 7.57 (1H, s), 7.65 (1H, d, J=7.2 Hz), 8.18 (1H, s). MS (ES) m/z: 333.1 [M+H].

Provenance & Evidence