Phosphorus oxychloride → HCID 117702910, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of N′-(3-methoxy-5-nitropyridin-2-yl)acetohydrazide (Step 84.2) (23.3 g, 84 mmol) in CH3CN (200 mL) was added DIEA (11.1 mL, 63.3 mmol) and dropwise POCl3 (11.8 mL, 127 mmol) and the reaction mixture was stirred for 3.5 hr at 90° C. The cooled mixture was slowly added to water (600 mL), stirred for 30 min before the mixture was neutralized with solid NaHCO3 to pH 6.5. The product was extracted with CH2Cl2/MeOH 6:1. Combined extracts were washed with H2O, dried over MgSO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (hexane/EtOAc/MeOH 50:50:5 to 0:50:5) followed by recrystallization from CH2Cl2/EtOAc/Et2O. tR: 0.49 min (LC-MS 2); ESI-MS: 209 [M+H]+ (LC-MS 2); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.79 (s, 3H) 4.10 (s, 3H) 7.29 (d, J=1.7 Hz, 1H) 9.25 (d, J=1.7 Hz, 1H).

Provenance & Evidence