Tetrahydrofuran → HCID 178434017, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(4-dimethylamino-piperidin-1-yl)-imidazo[4,5-b]pyridin-3-carboxylic acid tert-butyl ester (Step 1) (50 mg, 0.145 mmole), 2-(1,3,5-trimethyl-1H-pyrazol-4-yl-isonicotinic acid methyl ester (35 mg, 0.145 mmole), and tetrahydrofuran (3 ml) was cooled to −78° C. and reacted in accordance with General procedure J (LDA metallation), followed by work up method D. Thus, lithium diisopropylamide (2N, 0.15 ml, 0.30 mmole) was added slowly to the mixture which was stirred at −78° C. for 2 hours and then quenched with water. Solvent was removed and crude product was purified by using HPLC to afford [5-(4-dimethylamino-piperidin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl]-[2-(1,3,5-trimethyl-1H-pyrazol-4-yl)-pyridin-4-yl]-methanone (3 mg, 4.5%) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ 1.57 (m, 2H), 1.99 (m, 2H), 2.33 (s, 6H), 2.35 (s, 3H), 2.43 (s, 3H), 2.90 (m, 2H), 3.14 (m, 1H), 3.81 (s, 3H), 4.49 (m, 2H), 6.90 (d, J=9.03 Hz, 1H), 7.85 (d, J=9.03 Hz, 1H), 7.95 (d, J=5.02 Hz, 1H), 8.11 (s, 1H), 8.78 (d, J=5.02 Hz, 1H). MS(ESI) m/z 459 [M+1].

Provenance & Evidence