Diisopropylethylamine → HCID 70664841, compound

HRID 1403645Notes

Reaction equation

HRID 1403645 reaction equation
Cl[C:2]1[C:3](=[O:16])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.[CH2:17]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][NH:20]1)[CH3:18].CCN(C(C)C)C(C)C>CS(C)=O>[CH2:17]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][N:20]1[C:2]1[C:3](=[O:16])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2)[CH3:18]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 942052-EthylpiperidineHCID 68194304Methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Product 1

HCID 70664841HCID 70664841, compoundYield 22.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (500 mg, crude) in DMSO (5 mL) was added 2-ethylpiperidine (475 mg, 4.20 mmol) and DIEA (542 mg, 4.19 mmol). The resulting solution was stirred overnight at 80° C. in an oil bath and then quenched by the addition of water (50 mL), extracted with dichloromethane (5×20 mL). The organic layers were combined, dried over magnesium sulfate, and concentrated in vacuo to give a residue, which was purified via silica gel column chromatography (1%-10% ethyl acetate in petroleum ether) to afford methyl 3-(2-ethylpiperidin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as yellow oil (150 mg).

Workup

  1. customquenched by the addition of water (50 mL)
  2. extractionextracted with dichloromethane (5×20 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a residue, which
  6. customwas purified via silica gel column chromatography (1%-10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-6b10d6b68ac64030b5b6c3122da6f434
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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