1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-(1-(2-(6-Cyclopropylpyridin-2-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(2,5-dihydro-1H-pyrrol-1-yl)methanone

Participants

Reaction Steps

To a stirred solution of (R)-1-(2-(6-cyclopropylpyridin-2-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylic acid (150 mg, 0.686 mmol) in N,N-dimethylformamide (15 mL) was added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (150 mg, 0.826 mmol), hydroxybenzotriazole (111 mg, 0.826 mmol), and 3-pyrroline (57 mg, 0.826 mmol) at room temperature. The reaction mixture was stirred for 24 h at room temperature then poured into ice water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The crude material was purified via preparative TLC (80% ethyl acetate in petroleum ether) to afford the title compound (30 mg, 17%). MS (ES+APCI) (M+H) 415.0; LCMS retention time 2.493 min (Method G). 1H NMR (300 MHz, CDCl3) δ 1.09 (m, 4H), 1.70 (m, 2H), 1.90 (m, 3H), 2.09 (m, 1H), 2.69 (m, 1H), 3.02 (m, 1H), 3.16 (m, 1H), 4.28 (m, 3H), 4.51 (m, 2H), 5.84 (m, 1H), 5.93 (m, 1H), 6.71 (d, 1H), 7.20 (d, 1H), 7.66 (m, 1H), 7.87 (d, 1H), 8.04 (m, 1H), 10.18 (br s, 1H).

Provenance & Evidence