4-Piperidinecarboxamide → HCID 45275249, compound

HRID 1622357Notes

Reaction equation

HRID 1622357 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[NH:10]1[CH2:18][CH2:17][CH:13]([C:14]([NH2:16])=[O:15])[CH2:12][CH2:11]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C=O)C>[Br:1][C:2]1[C:3]([N:10]2[CH2:18][CH2:17][CH:13]([C:14]([NH2:16])=[O:15])[CH2:12][CH2:11]2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 37724-PiperidinecarboxamideHCID 8471TriethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 516892Sodium Bicarbonate

Product 1

HCID 45275249HCID 45275249, compoundYield 108.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-2,4-dichloropyrimidine (0.11 g, 0.50 mmol) and isonipecotamide (77 mg, 0.60 mmol) in DMF (2 mL) was added triethylamine (77 μL, 0.55 mmol) and the mixture was stirred at r.t. for 4.5 h. The mixture was poured into a saturated solution of sodium hydrogen carbonate (10 mL) and extracted with EtOAc (2×10 mL). The combined organic extracts were washed with water (10 mL), brine (10 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 (174 mg, 95%), m/z (ESI) C10H12BrClN4NaO requires 340.9775 found [M+Na]+ 340.9776.

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. washThe combined organic extracts were washed with water (10 mL), brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, 98:2)

Sources & evidence

ORD record
ord-182e4f3cd56a469c9833bb6bbdbdcc09
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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