Acetoacetic Acid → HCID 10123048, compound

Participants

Reaction Steps

To a room temperature solution of 4-{[3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-7-yl]amino}butan-1-ol (22 mg, 0.05 mmol) in dichloromethane (5 mL) was added 1-H-tetrazole (7 mg, 0.1 mmol) and dibenzyl N,N-diisopropylphosphoramidate (0.32 mL of a stock solution prepared from 0.2 mL of dibenzyl N,N-diisopropylphosphoramidate in 3.2 mL of dichloromethane). The resultant solution was stirred at room temperature for 1 hour and then cooled to 0° C. lodobenzene diacetate (16.5 mg, 0.05 mmol) was added and the mixture was stirred for 20 minutes. Saturated aqueous sodium thiosulfate and saturated aqueous sodium bicarbonate were added and the layers separated. The organic layer was washed with brine. The aqueous layer was extracted with dichloromethane and the combined organics were dried over sodium sulfate. Filtration and concentration followed by flash chromatography (1:4 hexanes-ethyl acetate) provided dibenzyl 4-{[3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-7-yl]amino}butyl phosphate (18 mg, 53%). 1H NMR (CDCl3): δ 8.03 (d, 1 H), 7.81 (d, 1 H), 7.61 (d, 2 H), 7.38–7.32 (m, 11 H), 7.01 (d, 2 H), 6.36 (d, 1 H), 6.06 (m, 1 H), 5.98 (d, 1 H), 5.13–5.01 (m, 5 H), 4.40 (m, 1 H), 4.05 (m, 2 H), 3.91 (s, 3 H), 3.37 (m, 2 H), 2.16–1.54 (m, 12 H); MS m/z 733 (M+1).

Provenance & Evidence