Potassium Carbonate → HCID 58368418, compound

HRID 1192666Notes

Reaction equation

HRID 1192666 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=[O:14])[CH3:13])[C:9]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:28][C:29]([N:31]([CH3:33])[CH3:32])=[O:30]>CN(C)C=O.ClCCl>[C:12]([C:10]1[C:9]([N:15]2[CH2:16][CH2:17][N:18]([CH2:28][C:29]([N:31]([CH3:33])[CH3:32])=[O:30])[CH2:19][CH2:20]2)=[C:8]2[C:3]([CH:4]=[CH:5][CH:6]=[N:7]2)=[C:2]([Cl:1])[CH:11]=1)(=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 67301190HCID 67301190, compound

Product 1

HCID 58368418HCID 58368418, compoundYield 50.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mix of 1-(5-chloro-8-piperazin-1-ylquinolin-7-yl)ethanone (0.030 g, 0.10 mmol, from Example 47, Step 1) and potassium carbonate (0.043 g, 0.31 mmol) in N,N-dimethylformamide (1 mL) was added 2-chloro-N,N-dimethylacetamide (0.012 mL, 0.11 mmol). The reaction mixture was stirred at room temperature for 4 hrs, and then diluted with dichloromethane, washed with water, dried over MgSO4, concentrated and purified on silica gel (eluting with 0 to 5% methanol in dichloromethane) to give the desired product (19 mg, 49%). LCMS calculated for C19H24ClN4O2 (M+H)+: m/z=375.2; Found: 375.1.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. custompurified on silica gel (eluting with 0 to 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-e1c42805f8cf47649384e8ecc1cf7928
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

Loading…