Ammonia → HCID 56597868, compound

Participants

Reaction Conditions

Reaction Steps

To a 10 mL microwave vial equipped with stir bar were added 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.060 g, 0.160 mmol), ethanol (1.5 mL), and 1,1-dimethylethyl 1-piperazinecarboxylate (0.299 g, 1.605 mmol). The stirring suspension was placed onto heat block and heated at 120° C. for 18 h, and then irradiated (microwave) at 160° C. for 2 hr. The contents were cooled to room temperature, diluted into water (40 mL), and then adjusted to pH 6-7 and stirred for 15 min. The contents were filtered, washed with water, and then dried in hi-vac oven at 50° C. for 5 hr. The collected solid (52 mg) was dissolved in CH2Cl2/TFA (3 mL, 2:1) and stirred at room temperature for 2 hr. The volatiles were removed in vacuo to afford a residue which was then dissolved in CH2Cl2 and 10% 2M Ammonia (in methanol) in Chloroform. The crude product was purified by silica gel chromatography (eluent: gradient of 10% 2M Ammonia (in Methanol/Chloroform) and Dichloromethane). The isolated solid was dried in vacuum oven at 45° C. for 18 hr. to afford the final product as 38 mg (55% yield). LCMS E-S (M+H)=423.9. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.43 (d, J=6.82 Hz, 6H), 2.08-2.24 (m, 6H), 2.75-2.89 (m, 4H), 3.53-3.64 (m, 4H), 4.34 (d, J=4.80 Hz, 2H), 4.98 (quin, J=6.69 Hz, 1H), 5.89 (s, 1H), 7.10 (s, 1H), 8.00 (s, 1H), 8.65 (t, J=4.93 Hz, 1H), 11.55 (br. s., 1H).

Provenance & Evidence