Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 178487832, compound

Participants

Reaction Conditions

Reaction Steps

O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.04 g, 2.73 mmol, 1.5 eq) is added at room temperature to a stirred solution of 3-(trans-4-tert-butoxycarbonylamino-cyclohexyl)-propionic acid (494 mg, 1.82 mmol, 1.0 eq) and 3-hydroxy-6-methoxy-quinoline-4-carbaldehyde (370 mg, 1.82 mmol, 1.0 eq) in N,N-dimethylformamide (20 mL), followed by 1,8-diazabicycloundec-7-ene (817 μL, 5.46 mmol, 3.0 eq). After 4 hours stirring at 50° C., solvent is evaporated and the residue is extracted with ethyl acetate (3×30 mL) and water (30 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 5:1 to 2:1, v/v) to afford [trans-4-(6-methoxy-2-oxo-2H-1-oxa-9-aza-phenanthren-3-ylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester as a yellow solid (270 mg, 34% yield).

Provenance & Evidence