Triethylamine → HCID 57863459, compound

Participants

Reaction Steps

Dissolve 4-(7-pyridin-4-yl-imidazo[1,2-a]pyridin-3-yl)-2-trifluoromethyl-phenylamine (0.4 g, 1.1 mmol) in DCM (40 mL) under nitrogen. Add triethylamine (0.39 mL, 2.5 equiv.) followed by careful addition of triphosgene (0.13 g, 0.4 equiv.). After 15 minutes at room temperature, add 5-tert-butyl-isoxazol-3-ylamine (0.19 g, 1.2 equiv.) and stir for 2 days at room temperature. Quench with water then dilute with ethyl acetate. Wash organics with 1 N NaOH followed by aqueous saturated sodium chloride. Dry organics over MgSO4 then filter and concentrate. Purify by reverse phase (5% MeCN:0.03% HCl in water→65% MeCN:0.03% HCl in water). Dilute product containing fractions with ethyl acetate then wash with 1 N NaOH followed by aqueous saturated sodium chloride. Dry the organics over MgSO4 then filter and concentrate to give the freebase (0.33 g off-white solid, 56%). MS (ES), m/z 521.1 (M+1).

Provenance & Evidence