Pyridine → N-(2-(piperidin-1-yl)phenyl)isoxazole-5-carboxamide

To PS-HOBt resin (0.1 mmol) was added anhydrous dichloromethane (“DCM”) (1 mL) followed by pyridine (0.5 mmol) and isoxazole-5-carbonyl chloride (Lancaster) (0.3 mmol). The mixture was shaken at room temperature for 3 h and was then filtered. The resin was washed successively with tetrahydrofuran (“THF”) (3×) and DCM (3×) and dried in vacuo. To this acylated resin was added a solution of 2-piperidinoaniline (Lancaster) (0.05 mmol, 0.5 eq) in anhydrous THF (1 mL) and the mixture was shaken at room temperature for 16 h. The mixtue was then filtered and the resin washed with THF and DCM as described above. The combined filtrate and washings were concentrated under reduced pressure to yield the product. Yield: 100%. MS: 272 (M+1). LC/MS purity: 100%. 1HNMR (CDCl3, 300 MHz): δ 8.2 (d, 1H), 7.85 (t, 2H), 7.55 (m, 1H), 7.4 (m, 2H), 3.8-3.2 (bm, 4H), 2.7-1.9 (bm, 4H).

1. filtrationwas then filtered
2. washThe resin was washed successively with tetrahydrofuran (“THF”) (3×) and DCM (3×)
3. customdried in vacuo
4. stirringthe mixture was shaken at room temperature for 16 h
5. filtrationThe mixtue was then filtered
6. washthe resin washed with THF and DCM
7. concentrationThe combined filtrate and washings were concentrated under reduced pressure
8. customto yield the product

ORD record

ord-b75a4ec6266647058e0dedf33493beb9

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07790724B2