Diethylamine → HCID 178463873, compound

HRID 1403359Notes

Reaction equation

HRID 1403359 reaction equation
Cl[C:2]1[C:3]([OH:16])=[N: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]([NH:19][CH2:20][CH3:21])[CH3:18].CCN(C(C)C)C(C)C>CS(C)=O.O>[CH2:17]([N:19]([CH2:20][CH3:21])[C:2]1[C:3]([OH:16])=[N: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

6

Reactant 3

HCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 178497332HCID 178497332, compound

Product 1

HCID 178463873HCID 178463873, compoundYield 30.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 3-chloro-2-hydroxyquinoxaline-6-carboxylate (450 mg, crude) in DMSO (5 mL) was added diethylamine (550 mg, 7.52 mmol), DIEA (492 mg, 3.81 mmol). After stirring for 2 h at 70° C., the resulting solution was diluted with water (50 mL), extracted with ethyl acetate (4×20 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a residue, which was purified by a silica gel column with 5% ethyl acetate in petroleum ether to afford methyl 3-(diethylamino)-2-hydroxyquinoxaline-6-carboxylate as a yellow solid (160 mg).

Workup

  1. extractionextracted with ethyl acetate (4×20 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto afford a residue, which
  5. customwas purified by a silica gel column with 5% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-ff71010df72c4cc3b44097ba71b77288
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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