Tetrahydrofuran → HCID 178482917, compound

Participants

Reaction Conditions

Reaction Steps

The mixture of 5-(4-dimethylamino-piperidin-1-yl)-imidazo[4,5-b]pyridin-3-carboxylic acid tert-butyl ester (Example 1) (50 mg, 0.145 mmole), 4-cyano-3-isoquinolin-4-yl-benzoic acid methyl ester (41 mg, 0.145 mmole), and tetrahydrofuran (3 ml) was cooled to −78° C. Lithium diisopropylamide (2N, 0.15 ml, 0.30 mmole) was added slowly. Reaction mixture was stirred at −78° C. for 2 hours and then was quenched with water, extracted with EtOAc. EtOAc layer was concentrated and crude product was purified by using HPLC (20% to 100% acetonitrile/water with 0.1% NH4OH) to afford 4-[5-(4-dimethylamino-piperidin-1-yl)-3H-imidazo[4,5-b]pyridine-2-carbonyl]-2-isoquinolin-4-yl-benzonitrile (2 mg, 3%) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ 1.59 (m, 2H), 1.98 (m, 2H), 2.31 (s, 6H), 2.44 (m, 2H), 3.14 (m, 1H), 3.02 (m, 2H), 4.50 (m, 2H), 6.86 (d, J=9.03 Hz, 1H), 7.00 (d, J=8.03 Hz, 1H), 7.78 (m, 2H), 7.89 (d, J=9.54 Hz, 1H), 8.08 (d, J=8.03 Hz, 1H), 8.18 (J=7.03 Hz, 1H), 8.62 (s, 1H), 8.81 (s, 1H), 8.86 (d, J=8.03 Hz, 1H), 9.43 (s, 1H). HR-MS m/z 502.2357 (M+1).

Provenance & Evidence