Benzaldehyde → HCID 78079303, compound

Participants

Reaction Conditions

Reaction Steps

Into a 50-mL round-bottom flask, was placed a solution of 3-[2-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-1,3-thiazolidine-2,4-dione (100 mg, 0.22 mmol, 1.00 equiv) in ethanol (20 mL) and benzaldehyde (47 mg, 0.44 mmol, 1.98 equiv) and piperidine (479.5 mg, 5.63 mmol, 25.14 equiv) were added. The resulting solution was stirred for 12 h at 70° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with dichloromethane/methanol (100/1) to give 31 mg (24%) of 3-[2-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-(phenylmethylidene)-1,3-thiazolidine-2,4-dione as a light yellow solid. LC-MS: (ES, m/z): 535 (M+H)

Provenance & Evidence