Cesium carbonate → HCID 178457858, compound

Participants

Reaction Conditions

Reaction Steps

A round-bottom flask under nitrogen was charged with 1-piperidineethanol (19.34 mL, 147 mmol), 18-crown-6 (11.63 g, 44.0 mmol), cis-4-(2-chloro-5-nitropyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide (10.00 g, 29.3 mmol), cesium carbonate (28.7 g, 88 mmol) and toluene (196 mL). The reaction mixture was purged with nitrogen and heated at 75° C. for 12 hours. The reaction mixture was diluted with EtOAc, and washed with brine, followed by saturated NH4Cl (aq). The aqueous layers were back-extracted with EtOAc, and the combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. The residual material was purified via silica gel chromatography eluting with isocratic 90:10:1 DCM:MeOH:NH4OH, to provide cis-N-isopropyl-4-(5-nitro-2-(2-(piperidin-1-yl)ethoxy)pyridin-4-ylamino)cyclohexanecarboxamide (10.79 g, 85% yield) as a rust-colored solid, which was taken forward without further purification. MS m/z=434.2 [M+H], calc 433.54 for C22H35N5O4.

Provenance & Evidence