Diisopropylethylamine → HCID 178497333, compound

HRID 1405264Notes

Reaction equation

HRID 1405264 reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][NH:3]1.Cl[C:9]1[C:10]([OH:23])=[N:11][C:12]2[C:17]([N:18]=1)=[CH:16][C:15]([C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=2.CCN(C(C)C)C(C)C>CS(C)=O.O>[OH:23][C:10]1[C:9]([N:3]2[CH2:4][CH2:5][O:6][CH2:7][C@@H:2]2[CH3:1])=[N:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=2)[N:11]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 12012220(3S)-3-methylmorpholineHCID 178497332HCID 178497332, compound

Product 1

HCID 178497333HCID 178497333, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (3S)-3-methylmorpholine (200 mg, 1.98 mmol) in DMSO (10 mL) was added methyl 3-chloro-2-hydroxyquinoxaline-6-carboxylate (700 mg, 2.93 mmol), DIEA (510 mg, 3.95 mmol). The resulting solution was stirred overnight at 70° C. and then dissolved in water (100 mL), extracted with dichloromethane (4×30 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by a silica gel column chromatography (5%-50% ethyl acetate in petroleum ether) to afford methyl 2-hydroxy-3-[(3S)-3-methylmorpholin-4-yl]quinoxaline-6-carboxylate as a light yellow solid (210.0 mg).

Workup

  1. extractionextracted with dichloromethane (4×30 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (5%-50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-09918fbfe9c14886acfbb515a7a83b17
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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