3-Isoxazolamine → HCID 117737238, compound

HRID 1504411Notes

Reaction equation

HRID 1504411 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][O:4][N:3]=1.[Br:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=1[N:18]1[C:27]2[C:22](=[CH:23][C:24]([S:28](Cl)(=[O:30])=[O:29])=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]1=[O:32].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[Br:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=1[N:18]1[C:27]2[C:22](=[CH:23][C:24]([S:28]([NH:1][C:2]3[CH:6]=[CH:5][O:4][N:3]=3)(=[O:30])=[O:29])=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]1=[O:32]

Participants

5

Reactant 3

HCID 18102163-IsoxazolamineHCID 2733832Lithium HexamethyldisilazideHCID 117737130HCID 117737130, compound

Product 1

HCID 117737238HCID 117737238, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-aminoisoxazole (0.380 ml, 5.14 mmol) and 1-(2-bromo-4-(trifluoromethyl)phenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonyl chloride (1.200 g, 2.57 mmol) in 10 mL THF was cooled to 0° C. and was treated with LHMDS 1N in THF (2.57 ml, 2.57 mmol). After stirring for 30 minutes, the reaction mixture was concentrated. Purification of the crude residue by reverse phase column chromatography [Puriflash C18, 10-100% (0.1% NH4OH in MeOH)/(0.1% NH4OH in water)] gave 1-(2-bromo-4-(trifluoromethyl)phenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.438 g, 0.852 mmol, 33.1% yield) with minor impurities. m/z (ESI) 514.0 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customPurification of the crude residue by reverse phase column chromatography [Puriflash C18, 10-100% (0.1% NH4OH in MeOH)/(0.1% NH4OH in water)]

Sources & evidence

ORD record
ord-b0397f9b281141b5a4b5faf546d0e651
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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