4-Piperidinecarboxamide → HCID 45275247, compound

To a solution of 5-bromo-4-chloropyrimidine hydrochloride 21 (0.10 g, 0.36 mmol) in DMF (2 mL) was added triethylamine (0.51 mL, 3.6 mmol). After stirring for 30 min, a solution of isonipecotamide (0.14 g, 1.1 mmol) in DMF (2 mL) was added and the mixture was stirred at r.t. for a further 16 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, 98:2) to furnish the title compound as a white solid (60 mg, 58%), m.p. 188-190° C.; umax (CHCl3)/cm−1 3012, 2853, 1682, 1566, 1447, 1359, 1144, 1017, 950; m/z (ESI) C10H14BrN4O requires 285.0346, found [M+H]+ 285.0344.

1. stirringthe mixture was stirred at r.t. for a further 16 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, 98:2)

ORD record

ord-0fe7ba06c2244c87a2882d2ce579189a

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778925B2