Sodium Nitrite → HCID 68523856, compound

Participants

Reaction Steps

To a solution of (S)—N6-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(4-fluorophenyl)ethyl)pyridine-2,3,6-triamine (Method 9; 0.08 g, 0.2 mmol), in aqueous acetic acid (5%, 3 ml) was slowly added the aqueous NaNO2 (0.01 g, 0.2 mmol, 1 ml H2O) solution at 25° C. The reaction was allowed to stir for an additional 5 minutes, then quenched with water (10 ml), and extracted with DCM (3×25 ml). The combined organic was washed with saturated NaHCO3 (50 ml), dried, filtered, and concentrated. The resulting solid was purified by column chromatography (DCM:MeOH=40:1) to give the title compound (0.037 g, 50%). NMR (400 MHz, CD3OD) 8.02 (d, J=8.9 Hz, 1H), 7.46-7.42 (m, 2H), 7.08-7.04 (m, 2H), 6.91 (d, J=8.9 Hz, 1H), 6.23-6.19 (m, 2H), 2.12 (d, J=7.0 Hz, 3H), 1.95-1.91 (m, 1H), 1.02-1.00 (m, 2H), 0.75-0.72 (m, 2H). MS: Calcd.: 363. Found: [M+H]+ 364.

Provenance & Evidence