Dimethylformamide → HCID 86685306, compound

Participants

Reaction Conditions

Reaction Steps

To 7-(1-methyl-1H-pyrazol-4-yl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (Preparation K; 50 mg, 0.19 mmol) was added DMF (950 μL, 0.19 mmol), tert-butyl 4-(2-cyanovinyl)piperidine-1-carboxylate (Table 1, compound 1; 67 mg, 0.28 mmol) and DBU (185 μL, 1.3 mmol). The reaction mixture was heated to 45° C. for 8 hours, then diluted in EtOAc and washed with water and brine. The organic layer was dried with MgSO4, filtered and concentrated down to a yellow oil. Purification of the resulting crude material by reverse phase HPLC using a 0-100% acetonitrile/water gradient afforded tert-butyl 4-(2-cyano-1-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)ethyl)piperidine-1-carboxylate (59 mg, 62% yield). MS (apci) m/z=502.2 (M+H).

Provenance & Evidence