4-Piperidinecarboxamide → HCID 45275246, compound

HRID 1622354Notes

Reaction equation

HRID 1622354 reaction equation
Cl.Cl[C:3]1[C:8]([Cl:9])=[CH:7][N:6]=[CH:5][N:4]=1.C(N(CC)CC)C.[NH:17]1[CH2:25][CH2:24][CH:20]([C:21]([NH2:23])=[O:22])[CH2:19][CH2:18]1.C(=O)([O-])O.[Na+]>CN(C=O)C>[Cl:9][C:8]1[C:3]([N:17]2[CH2:25][CH2:24][CH:20]([C:21]([NH2:23])=[O:22])[CH2:19][CH2:18]2)=[N:4][CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 37724-PiperidinecarboxamideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 86656267HCID 86656267, compound

Product 1

HCID 45275246HCID 45275246, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4,5-dichloropyrimidne hydrochloride 20 (0.20 g, 1.1 mmol) in DMF (4 mL) was added triethylamine (1.5 mL, 10 mmol). After stirring for 30 min, a solution of isonipecotamide (0.42 mg, 3.3 mmol) in DMF (4 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, gradient 98:2-96:4) to furnish the title compound as a white solid (51 mg, 20%), m.p. 201-202° C.; umax (CHCl3)/cm−1 3023, 3014, 1724, 1682, 1448, 1360, 1219, 1037; m/z (ESI) C10H14CN4O requires 241.0851, found [M+H]+ 241.0851.

Workup

  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, gradient 98:2-96:4)

Sources & evidence

ORD record
ord-5aa7f8aaccd344d784f7c4db6f7f2372
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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