4,7-Dichloroquinoline → HCID 21101685, compound

HRID 1353497Notes

Reaction equation

HRID 1353497 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]([NH:20][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]([NH:20][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])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 68664,7-DichloroquinolineHCID 9237DabcoHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamate

Product 1

HCID 21101685HCID 21101685, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a method similar to Example A 4,7-dichloroquinoline (0.49 g, 2.0 mmol), 3-(tert-butoxycarbonylamino)pyrrolidine (1.86 g, 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 245 mg of the 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 245 mg of the product as a colorless solid

Sources & evidence

ORD record
ord-5fc71c92cdfb47448ec1e1502c84c5c5
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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