Diisopropylethylamine → HCID 11853712, compound

Participants

Reaction Steps

Combine [2-fluoro-4-(7-pyridin-2-yl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-acetic acid, dihydrochloride (0.500 g, 1.19 mmol) and 5-tert-Butyl-4-morpholin-4-ylmethyl-thiazol-2-ylamine (0.334 g, 1.31 mmol) in DMF (6 mL). Add N,N-diisopropyl-ethylamine (0.54 mL, 3.93 mmol), then O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetra-methyluronium hexafluorophosphate (0.498 g, 1.31 mmol). The reaction mixture is stirred over the weekend under N2. Purify using an SCX cartridge (10 g VARIAN BondElut®), eluting with 1:1 methanol:dichloromethane, then 1:1 2 M NH3 in methanol:dichloromethane. Concentrate the latter and purify via reverse phase chromatography using a 25 cm by 50.8 mm (i.d.) column w/10 micron particles (MeCN/0.03% HCl H2O (5:95) to 100% MeCN; 30 min). Partition between ethyl acetate and 1 N NaOH. Dry the organic layer over magnesium sulfate, filter, and concentrate to the title compound (0.190 g, 27%). MS(ES), m/z 585 (M+1).

Provenance & Evidence