4-Piperidinecarboxamide → HCID 45275248, compound

To a solution of 5-methyl-4-chloropyrimidne hydrochloride 22 (75 mg, 0.45 mmol) in DMF (2 mL) was added triethylamine (0.63 mL, 4.5 mmol). After stirring for 15 min, a solution of isonipecotamide (64 mg, 0.50 mmol) in DMF (2 mL) was added and the mixture was stirred at r.t. for a further 20 h. The mixture was poured into a saturated solution of sodium hydrogen carbonate (50 mL) and extracted with EtOAc (2×25 mL). The combined organic extracts were washed with water (25 mL), brine (25 mL), dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, gradient 98:2 to 9:1) to furnish the title compound as a white solid (25 mg, 25%), m.p. 182-184° C.; umax (CHCl3)/cm−1 3024, 1678, 1581, 1439, 1359, 1147, 948; m/z (ESI) C11H17N4O requires 221.1397, found [M+H]+ 221.1394.

1. stirringthe mixture was stirred at r.t. for a further 20 h
2. extractionextracted with EtOAc (2×25 mL)
3. washThe combined organic extracts were washed with water (25 mL), brine (25 mL)
4. dry with materialdried (MgSO4)
5. concentrationconcentrated under reduced pressure
6. customThe crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, gradient 98:2 to 9:1)

ORD record

ord-41c6d32ee9e34ce298d236eb03022f3e

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778925B2