1-Hydroxybenzotriazole → 3-cyclopentyl-N-(5-methoxy-thiazolo[5,4-b]pyridin-2-yl)-2-[4-(2-oxo-propane-1-sulfonyl)-phenyl]-propionamide

Participants

Reaction Conditions

Reaction Steps

To a solution of the title D compound, 3-cyclopentyl-2-[4-(2-oxo-propylsulfonyl)-phenyl]-propionic acid (400 mg, 0.0011 mol) in 50 mL of DCM, HOBt (250 mg, 0.0018 mol), EDCl hydrochloride (340 mg, 0.0017 mol) and 5-methoxy-thiazolo[5,4-b]pyridin-2ylamine (235 mg, 0.0012 mol) are added followed by the addition of 0.66 mL (0.0037 mol) of DIEA. The reaction is stirred at 25° C. for 24 h, then worked up by treating it with saturated aqueous sodium bicarbonate solution. The resulting organic layer is washed with 1 N aqueous hydrochloric acid solution, followed by water and brine washings. The organic layer is dried over sodium sulfate, filtered and then evaporated under vacuum to give a brown solid. The reaction product is purified by column chromatography over Silica gel (60-120 mesh) using 80% hexane in ethyl acetate as an eluent to give 3-cyclopentyl-N-(5-methoxy-thiazolo[5,4-b]pyridin-2-yl)-2-[4-(2-oxo-propane-1-sulfonyl)-phenyl]-propionamide as a brown solid: MS e/z (ES) 502 (M+1+, 100%); m.p. 67-71° C.; 1H NMR δ 12.71 (s, 1H), 8.02 (d, J=8.8, 1H), 7.65-7.90 (m, 4H), 6.91 (d, J=8.8, 1H), 4.69 (s, 2H), 4.08-4.12 (m, 1H), 3.90 (s, 3H), 2.19 (s, 3H), 1.78-1.82 (m, 1H), 1.60-1.75 (m, 2H), 1.43-1.55 (m, 3H), 1.30-1.42 (m, 3H), 1.00-1.20 (m 2H).

Provenance & Evidence