Pyridine → HCID 178481622, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottomed flask was added N2-(cis-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-N3-methylpyrazine-2,3-diamine (0.1100 g, 0.337 mmol) and pyridine (0.082 mL, Sigma-Aldrich Chemical Company, Inc.) in DCM (1.1 mL) to stir at −40° C. for 30 mins. Triphosgene (0.120 g, 0.404 mmol, Sigma-Aldrich Chemical Company, Inc.) was added to stir for 30 mins. The temperature was brought to 0° C. and allowed to stir for 5 h. The reaction mixture was diluted with saturated sodium bicarbonate and extracted with CH2Cl2. The organic extract was washed with water, saturated NaCl, dried over MgSO4, filtered and concentrated in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (25 g), eluting with a gradient of 40% to 100% EtOAc in hexane, to provide the title compound (0.0352 g, 0.100 mmol, 29.6% yield). LCMS showed product peak at 1.51 min (m+1=353.0). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.72-2.85 (m, 1 H) 2.94-3.08 (m, 1 H) 3.34 (s, 2 H) 4.14-4.28 (m, 1 H) 4.62-4.76 (m, 1 H) 6.98-7.07 (m, 1 H) 7.19-7.26 (m, 1 H) 7.40 (d, J=7.43 Hz, 1 H) 7.64-7.71 (m, 1 H) 7.98 (s, 1 H) 8.52 (d, J=6.65 Hz, 1 H)

Provenance & Evidence