Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 86658644, compound

Participants

Reaction Steps

HATU (114.1 mg) was added to a 1 mL DMF solution of lithium 4-(3-amino-4-formylphenoxy)-butanoate (68.7 mg), and the reaction was shaken at room temperature for 1 hour. The resulting solution was then added to a 1 mL DMF solution of 4-nitrobenzylamine HCl salt (56.6 mg) and triethylamine (84 μL), with another 1 mL DMF to help transfer. The reaction was stirred at room temperature for 2 hours. Upon completion, the reaction mixture was partitioned between 4 mL of 10% NaCl(aq) and 8 mL of EtOAc. The phases were separated and the aqueous layer was extracted again with 8 mL EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure, affording a crude orange oil. The crude oil was purified by silica gel flash column chromatography with gradient elution of 0-10% MeOH/DCM to give the desired product as a light yellow solid. MS (ESI+): m/z 358.2. 1H NMR (400 MHz, CDCl3): 9.70 (s, 1H), 8.14 (d, J=8.8 Hz, 2H), 7.40 (d, J=8.8 Hz, 2H), 7.35 (d, J=8.4 Hz, 1H), 6.26 (dd, J=2.2 Hz, 8.8 Hz, 1H), 6.20 (br, 2H), 6.03 (d with br, J=2.0 Hz, 2H), 4.54 (d, J=6.0 Hz, 2H), 4.02 (t, J=5.8 Hz, 2H), 2.47 (t, J=7.0 Hz, 2H), 2.17 (quintet, J=6.5 Hz, 2H). 13C NMR (100 MHz, CDCl3): 192.0, 172.2, 164.4, 152.2, 147.2, 145.8, 137.8, 128.2, 123.9, 113.9, 105.3, 98.9, 66.7, 42.8, 32.5, 24.8.

Provenance & Evidence