Dichloromethane → HCID 78079304, compound

Participants

Reaction Steps

Into a 50-mL scaled tube, 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 methanol (20 mL), cyclopropanecarbaldehyde (47 mg, 0.67 mmol, 2.99 equiv), piperidine (9.5 mg, 0.11 mmol, 0.50 equiv), dichloromethane (5 mL). The resulting solution was stirred overnight at room temperature. 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 28 mg (24%) of 3-[2-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-(cyclopropylmethylidene)-1,3-thiazolidine-2,4-dione as a white solid. LC-MS (ES, m/z): 499 (M+H)+

Provenance & Evidence