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Diisopropylethylamine → Methyl 3-(cyclopropyl(methyl)amino)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

HRID 1403425
Notes
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Reaction equation

HRID 1403425 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.Cl.[CH3:18][NH:19][CH:20]1[CH2:22][CH2:21]1.CCN(C(C)C)C(C)C>CS(C)=O>[CH:20]1([N:19]([CH3:18])[C:2]2[C:3](=[O:16])[NH:4][C:5]3[C:10]([N:11]=2)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=3)[CH2:22][CH2:21]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 18546974N-methylcyclopropanamine hydrochlorideHCID 68194304Methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Product 1

HCID 70654244Methyl 3-(cyclopropyl(methyl)amino)-2-oxo-1,2-dihydroquinoxaline-6-carboxylateYield 86.3%

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Conditions

Temperature
75 °C

Procedure

To a solution of methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (300 mg, 1.26 mmol) in DMSO (2 mL), was added N-methylcyclopropanamine hydrochloride (175 mg, 1.63 mmol) and DIEA (325 mg, 2.52 mmol) with stirring for 2 h at 75° C. in an oil bath. Then the reaction was quenched by the addition of water (10 mL) to give the precipitate, which was collected by filtration to afford methyl 3-[cyclopropyl(methyl)amino]-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as an off-white solid (297 mg, 86%).

Workup

  1. customThen the reaction was quenched by the addition of water (10 mL)
  2. customto give the precipitate, which
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-e0c1929c12804ddbb92ec2671bafe67b
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08912188B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes