Dimethylformamide → HCID 178473710, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with (2S,4R)-1-acetyl-6-ethynyl-2-methyl-N-(6-methyl-2-pyridinyl)-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see Intermediate 112) (90 mg, 0.282 mmol) and copper(I) iodide (5.37 mg, 0.028 mmol) then filled with N,N-dimethylformamide (DMF) (0.9 mL) and methanol (0.100 mL) and the resulting mixture was treated with trimethylsilyl azide (0.150 mL, 1.127 mmol). The flask was flushed with nitrogen then the mixture was stirred at 100° C. for 1 hr under microwave irradiation then cooled to room temperature. Most of the methanol was removed in vacuo and the remaining organic phase was purified by MDAP (modifier: ammonium bicarbonate) to give (2S,4R)-1-acetyl-2-methyl-N-(6-methyl-2-pyridinyl)-6-(1H-1,2,3-triazol-4-yl)-1,2,3,4-tetrahydro-4-quinolinamine (3 mg, 8.28 μmol, 2.94% yield) as a colourless glass.

Provenance & Evidence