Nitrogen → HCID 67958869, compound

Participants

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 2-methyl-5-(m-tolyl)oxazole-4-carboxylic acid (WO 2009/077990) (92 mg, 0.42 mmol) in CH2Cl2 (2.0 mL) was treated successively with DMAP (13 mg, 0.11 mmol), HOBt (69 mg, 0.51 mmol), EDC.HCl (203 mg, 1.06 mmol) and DIPEA (0.29 mL, 1.69 mmol) and the mixture was stirred at rt for 30 min. A solution of 1-(2-((4-amino-2H-1,2,3-triazol-2-yl)methyl)oxazol-4-yl)cyclopropyl pivalate (129 mg, 0.42 mmol) in CH2Cl2 (2.0 mL) was then added and the reaction mixture was stirred at rt overnight. The reaction mixture was then diluted with CH2Cl2 (10 mL), the layers were separated and the org. layer was washed with water (10 mL), dried over MgSO4, filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (2:1 hept-EA) gave the title compound as a white foam: TLC: rf (2:1 hept-EA)=0.25. LC-MS-conditions 06: tR=1.10 min, [M+H]+=505.37.

Provenance & Evidence