20% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 5h; |
N-(6-aminopyridin-3-ylV2,6-difluoro-3-(propylsulfonamido)benzamide [00232] Diisopropylethylamine (0.266 mL, 1.53mmol), <strong>[1103234-56-5]2,6-difluoro-3-(propylsulfonamido)benzoic acid</strong> (77 mg, 0.275 mmol), hydroxybenzotriazole monohydrate (46.7 mg, 0.305 mmol) and l-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (59.6 mg, 0.336 mmol) were added to 2,5-diaminopyridine dihydrochloride (50 mg, 0.275 mmol) in dichloromethane (3 mL) and N,N-dimethylformamide (1 mL). The resulting mixture was stirred at ambient temperature. After 5 hours, the reaction mixture was diluted with brine and extracted twice with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried over magnesium sulfate, filtered, and evaporated to yield crude product (70 mg) as a film. This was chromatographed on a silica gel plug, eluting with 4:1 ethyl acetate :methanol. Fraction 2 contained solid (20.3 mg, yield 20%). 1H NMR (400 MHz, CD3OD) delta 8.17 (s, IH), 7.79-7.75 (m, IH), 7.66-7.59 (m, IH), 7.10 (t, IH), 6.62 (d, IH), 3.09 (t, 2H), 1.91-1.81 (m, 2H), 1.05 (t, 3H); m/z (APCI pos) 371.1 (100%) [M+l]. |