Dimethylformamide → 4-[3-((2S,6R)-2,6-Dimethyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-cyclohexylamine

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Reaction Steps

Sodium hydride (60% in mineral oil, 0.26 g, 6.39 mmol) was added to a stirred solution of trans-4-amino cyclohexanol (0.397 g, 3.45 mmol) in anhydrous DMF (10 mL) at RT under an argon atmosphere. The reaction mixture was stirred at RT for 30 min, then Intermediate 2d (0.50 g, 2.13 mmol) in anhydrous DMF (4 mL) was added and stirred at 60° C. for 10 h. After cooling, the reaction mixture was quenched by careful addition of a saturated aqueous solution of NH4Cl and water (1:1) and extracted with EtOAc and then DCM. The combined organic extracts were concentrated in vacuo and the resultant residue was purified by FCC, using 0-25% [2M NH3 in MeOH] in DCM, to afford the title compound (0.193 g, 27%) as an orange residue. LCMS (Method 3): Rt 2.00 min, m/z 330 [MH+].

Provenance & Evidence