1,4-Dioxane → HCID 178434141, compound

Participants

Reaction Conditions

Reaction Steps

The mixture of [4-[2-(2-bromo-pyridine-4-carbonyl)-3H-imidazo[4,5-b]pyridine-5-yl]-piperazine-1-carboxylic acid tert-butyl ester (Example 164) (100 mg, 0.205 mmole), 3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazole-1-carboxylic acid tert-butyl ester (Example 167) (66 mg, 0.205 mmole), Pd(Ph3)4 (23 mg, 0.021 mmole), 2 molar of K3PO4 aqueous (0.21 ml, 0.41 mmole), and dioxane (3.0 ml) was degassed and heated to 120° C. for 40 minutes in microwave. Reaction solution was diluted with water and extracted with EtOAc. EtOAc layer was concentrated to afford 120 mg of crude 4-{2-[2-(1-tert-butoxycarbonyl-3,5-dimethyl-1H-pyrazol-4-yl)-pyridine-4-carbonyl]-3H-imidazo[4,5-b]pyridin-5-yl}-piperazine-1-carboxylic acid tert-butyl ester, which was dissolved in 3 ml of 2 molar HCl ether solution. The acidic solution was stirred for 2 hours, then solvent was removed. Residue was washed with EtOAc and was purified by using HPLC, eluting with 10 to 20% of acetonitrile in water (0.1% of NH4OH) to yield [2-(3,5-Dimethyl-1H-pyrazol-4-yl)-pyridin-4-yl]-(5-piperazin-1-yl-3H-imidazo[4,5-b]pyridine-2-yl)-methanon (20 mg, 24%) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ 2.41 (s, 6H), 2.94 (m, 4H), 3.61 (m, 4H), 6.88 (d, J=9.03 Hz, 1H), 7.87 (d, J=9.03 Hz, 1H), 7.94 (d, J=5.02 Hz, 1H), 8.17 (s, 1H), 8.76 (d, J=5.02 Hz, 1H). HR-MS m/z 403.1981 (M+1).

Provenance & Evidence