Chloroacetyl chloride → HCID 66958547, compound

HRID 1364024Notes

Reaction equation

HRID 1364024 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])([CH3:16])[CH3:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:22](N(CC)CC)[CH3:23].ClCC(Cl)=O>ClCCCl>[CH3:16][C:14]1([CH3:15])[N:17]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:23][C:22]2=[N:1][C:2]3[CH:3]=[N:4][C:5]4[C:10]([C:11]=3[N:12]2[CH2:13]1)=[CH:9][CH:8]=[CH:7][CH:6]=4

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66958650HCID 66958650, compound

Product 1

HCID 66958547HCID 66958547, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Under a nitrogen atmosphere, a solution of N-{2-[(3-aminoquinolin-4-yl)amino]-1,1-dimethylethyl}methanesulfonamide (2.65 g, 8.59 mmol) in 1,2-dichloroethane (100 mL) was cooled to 0° C. Triethylamine (2.4 mL, 17 mmol) and chloroacetyl chloride (0.82 mL, 10.3 mmol) were sequentially added, and the reaction was allowed to warm to ambient temperature, stirred overnight, and then heated at reflux for 1.5 days. The reaction was washed with saturated aqueous sodium bicarbonate (2×100 mL) and brine (100 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 1.92 g of 10,10-dimethyl-9-(methylsulfonyl)-8,9,10,11-tetrahydropyrazino[4′,3′:1,2]imidazo[4,5-c]quinoline as a brown solid, which was used without purification.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.5 days
  3. washThe reaction was washed with saturated aqueous sodium bicarbonate (2×100 mL) and brine (100 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d2304b8e62d84da196b931226dff50ac
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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