3-(Pyrrolidin-2-yl)pyridine → HCID 87464498, compound

Participants

Reaction Steps

A solution of (Z)-3-methyl-1-(5-methyl-3-(2,2,3,3-tetrafluoro-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)thiazol-2(3H)-ylidenecarbamoyl)-1H-imidazol-3-ium iodide core (Example 81A, 0.88 mL of 0.16 M in acetonitrile, 80 mg, 0.1 mmol) was added to a 20 mL vial, followed by N,N-diisopropylethylamine (0.88 mL of 0.2 M in acetonitrile, 24 mg, 0.13 mmol). 3-(Pyrrolidin-2-yl)pyridine (0.79 mL of 0.2 M in acetonitrile, 0.11 mmol) was added last. The resulting mixture was shaken at room temperature overnight. It was then concentrated in vacuo, and the residue was taken up in 1:1 MeOH/DMSO and purified by reverse phase HPLC (acetonitrile/water 0.1% TFA gradient elution method) to give the titled compound. 1H NMR (300 MHz, DMSO-d6/D2O) δ ppm 1.74-1.93 (3 H) 2.12-2.21 (3 H) 2.33-2.44 (1 H) 3.50-3.68 (2 H) 4.95-5.07 (1 H) 6.91-7.06 (1 H) 7.21-7.59 (3 H) 7.70-7.91 (1 H) 8.33-8.42 (1 H) 8.44-8.52 (1 H); MS (ESI+) m/z 495 (M+H).

Provenance & Evidence