2,3-Dichloroquinoxaline → HCID 86678190, compound

HRID 1747517Notes

Reaction equation

[CH3:1][C:2]1([CH:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[OH:6])[CH2:4][CH2:3]1.[Cl:13][C:14]1[C:23](Cl)=[N:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1.[H-].[Na+].[Cl-].[NH4+]>C1COCC1.O>[Cl:13][C:14]1[C:23]([O:6][CH:5]([C:2]2([CH3:1])[CH2:4][CH2:3]2)[C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1

Participants

Conditions

Temperature: 50 °C

Procedure

In THF (5.0 mL) were dissolved (1-methylcyclopropyl)(pyridin-3-yl)methanol (130 mg, 0.796 mmol) obtained in Step 2 and 2,3-dichloroquinoxaline (190 mg, 0.956 mmol). To the mixture was added 60% sodium hydride (in oil, 38.2 mg, 0.956 mmol) and the mixture was stirred at 50° C. for 1.5 hours. A saturated aqueous ammonium chloride solution and water were added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=17/3) to give Compound A9 (147 mg, 57% yield).

Workup

extractionExtraction with ethyl acetate
washwashing with saturated brine
dry with materialdrying over anhydrous sodium sulfate
filtrationAfter filtration
customthe solvent in the filtrate was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=17/3)

Sources & evidence

ORD record: ord-20ff03164a8e4d74ae94313b625e0d9f
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150569B2

Reaction notes

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