Trifluoroacetic acid → 3-methyl-N-(4-{[2-(1H-pyrrol-2-yl)pyridin-4-yl]oxy}phenyl)-2-furamide

Temperature

45 °C

A mixture of 3-methyl-2-furoic acid (70 mg, 0.55 mmol), HATU (243 mg, 0.64 mmol), tert-butyl 2-[4-(4-aminophenoxyl)pyridin-2-yl]-1H-pyrrole-1-carboxylate (160 mg, 0.46 mmol) and N,N-diisopropylethylamine (148 mg, 1.15 mmol) in anhydrous DMF (10 ml) was stirred at 45° C. for 2 hours. The mixture was poured into 100 ml of water. The precipitates were filtered, washed with water and dried in vacuo to give the crude, which was dissolved in 5 ml of methylene chloride, followed by addition of trifluoroacetic acid (3 ml). The mixture was stirred at room temperature for 16 hours. The solvents were evaporated under reduced pressure. The residue was purified by reversed-phase chromatography with a gradient of 10˜50% acetonitrile/water to give 3-methyl-N-(4-{[2-(1H-pyrrol-2-yl)pyridin-4-yl]oxy}phenyl)-2-furamide as white solid. Yield: 56 mg, 34%.

1. filtrationThe precipitates were filtered
2. washwashed with water
3. customdried in vacuo
4. customto give the crude, which
5. stirringThe mixture was stirred at room temperature for 16 hours
6. customThe solvents were evaporated under reduced pressure
7. customThe residue was purified by reversed-phase chromatography with a gradient of 10˜50% acetonitrile/water

ORD record

ord-bef90fb83daf44a6831c4bb3c88c8590

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09328103B2