4,7-Dichloroquinoline → HCID 21101686, compound

HRID 1353499Notes

Reaction equation

HRID 1353499 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[C:13]([O:17][C:18]([N:20]([CH3:26])[CH:21]1[CH2:25][CH2:24][NH:23][CH2:22]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].N12CCN(CC1)CC2>CCO>[C:13]([O:17][C:18]([N:20]([CH3:26])[CH:21]1[CH2:25][CH2:24][N:23]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)[CH2:22]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 68664,7-DichloroquinolineHCID 9237DabcoHCID 27614043-(N-tert-Butoxycarbonyl-N-methylamino)pyrrolidine

Product 1

HCID 21101686HCID 21101686, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4,7-Dichloroquinoline (0.49 g, 2.0 mmol), 3-[tert-butoxycarbonyl(methyl)amino]pyrrolidine (1.96 mL, 10.0 mmol) and 1,4-diazabicyclo[2.2.2]octane (1.12 g, 10.0 mmol) are heated in EtOH for 15 h at reflux. The reaction mixture is concentrated, diluted with EtOAc, washed with water, dried (MgSO4), and concentrated. The residue is purified by column chromatography with hexane-EtOAc yielding the title product as a colorless solid.

Workup

  1. temperatureat reflux
  2. concentrationThe reaction mixture is concentrated
  3. additiondiluted with EtOAc
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue is purified by column chromatography with hexane-EtOAc yielding the title product as a colorless solid

Sources & evidence

ORD record
ord-a2ea28908107421ab0de097ecc3dcbd7
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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