Diisopropylethylamine → 2,5-dichloro-N-[2-[2-(2,5-difluorophenyl)ethoxy]ethanimidoyl]pyridine-3-carboxamide

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Reaction Steps

2,5-Dichloronicotinic acid (50 mg, 260 μmol), TBTU (88 mg, 273 μmol) and DIPEA (130 μl, 781 μmol) were added to a solution of 2-[2-(2,5-difluoro-phenyl)-ethoxy]-acetamidine hydrochloride (65 mg, 260 μmol) in DMF (1 ml). The solution was stirred for 72 h at ambient temperature and poured onto ice water/dichloromethane 1/1. The layers were separated, the aqueous layer was extracted two times with dichloromethane, the combined extracts were washed with brine and dried over sodium sulfate. Removal of the solvent under reduced pressure yielded 2,5-dichloro-N-{2-[2-(2,5-difluoro-phenyl)-ethoxy]-1-imino-ethyl}-nicotinamide (97 mg, 250 μmol; 96%) as orange oil which was used in the next step without further purification. MS: m/e=388.2 [M+H+].

Provenance & Evidence