1,4-Dioxane → HCID 117737169, compound

HRID 1504416Notes

Reaction equation

HRID 1504416 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][O:4][N:3]=1.[Br:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([S:25](Cl)(=[O:27])=[O:26])=[CH:22][CH:23]=3)[C:18]([CH3:29])=[CH:17][C:16]2=[O:30])=[C:10]([O:31][CH3:32])[CH:9]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.O1CCOCC1>C1COCC1>[Br:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([S:25]([NH:1][C:2]4[CH:6]=[CH:5][O:4][N:3]=4)(=[O:26])=[O:27])=[CH:22][CH:23]=3)[C:18]([CH3:29])=[CH:17][C:16]2=[O:30])=[C:10]([O:31][CH3:32])[CH:9]=1

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 18102163-IsoxazolamineHCID 2733832Lithium HexamethyldisilazideHCID 117736990HCID 117736990, compound

Product 1

HCID 117737169HCID 117737169, compoundYield 24.92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-aminoisoxazole (0.867 ml, 11.74 mmol) and 1-(4-bromo-5-chloro-2-methoxyphenyl)-4-methyl-2-oxo-1,2-dihydroquinoline-6-sulfonyl chloride (1.120 g, 2.347 mmol) in 10 mL THF, was cooled to 0° C. LHMDS 1N in THF (11.74 ml, 11.74 mmol) was added, and the cooling bath was removed. After stirring for an additional hour, the reaction mixture was treated with hcl 4N in dioxane (5.87 ml, 23.47 mmol) and was concentrated. Purification of the crude residue by reverse phase column chromatography [Redisep Gold C18, 10-100% (0.1% NH4OH in MeOH)/(0.1% NH4OH in water)] gave 1-(4-bromo-5-chloro-2-methoxyphenyl)-N-(isoxazol-3-yl)-4-methyl-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.307 g, 0.585 mmol, 24.92% yield). In/z (ESI) 525.9 (M+H)+.

Workup

  1. customthe cooling bath was removed
  2. concentrationwas concentrated
  3. customPurification of the crude residue by reverse phase column chromatography [Redisep Gold C18, 10-100% (0.1% NH4OH in MeOH)/(0.1% NH4OH in water)]

Sources & evidence

ORD record
ord-d3c112d5b90c4a0baa12bf5b8a14fbc0
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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