Sodium hydride → HCID 21101814, compound

HRID 1353326Notes

Reaction equation

HRID 1353326 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[CH2:7][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([C:6]2[C:5]3[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 69515221HCID 69515221, compound

Product 1

HCID 21101814HCID 21101814, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 7-chloro-4-quinolone-2-carboxylate (1.0 g, 4 mmol) is stirred with sodium hydride (0.144 g, 6 mmol) in DMF (50 mL) for 1 h at 40° C. N-Phenyl (trifluoromethylsulfon)imide (2.0 g, 5.6 mmol) is added and, after an hour, 1-tert-butoxycarbonylpiperazine (3.0 g, 6 mmol). The reaction mixture is stirred at 50° C. for 15 h, concentrated, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and concentrated. The residue is purified by column chromatography with CH2Cl2-MeOH yielding the title product as a colorless solid.

Workup

  1. concentrationconcentrated
  2. additiondiluted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography with CH2Cl2-MeOH yielding the title product as a colorless solid

Sources & evidence

ORD record
ord-117ba2767891451aa17372cbfc58b529
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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