Tetrahydrofuran → HCID 117736877, compound

HRID 1504425Notes

Reaction equation

HRID 1504425 reaction equation
[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([S:20](OC4C(F)=C(F)C(F)=C(F)C=4F)(=[O:22])=[O:21])=[C:16]([F:19])[CH:17]=3)[CH:12]=[CH:11][C:10]2=[O:35])=[C:4]([O:36][CH3:37])[CH:3]=1.[NH2:38][C:39]1[CH:43]=[CH:42][O:41][N:40]=1.C1COCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>Cl.CCOC(C)=O>[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([S:20]([NH:38][C:39]4[CH:43]=[CH:42][O:41][N:40]=4)(=[O:22])=[O:21])=[C:16]([F:19])[CH:17]=3)[CH:12]=[CH:11][C:10]2=[O:35])=[C:4]([O:36][CH3:37])[CH:3]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 18102163-IsoxazolamineHCID 2733832Lithium HexamethyldisilazideHCID 117737030HCID 117737030, compound

Product 1

HCID 117736877HCID 117736877, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of perfluorophenyl 1-(4-bromo-5-chloro-2-methoxyphenyl)-7-fluoro-2-oxo-1,2-dihydroquinoline-6-sulfonate (0.440 g, 0.700 mmol), 3-aminoisoxazole (0.057 ml, 0.770 mmol) and THF (7.0 ml) was cooled in an ice-bath for 15 min, then lithium bis(trimethylsilyl)amide (1M in TI-IF) (1.47 ml, 1.47 mmol) was added dropwise. After 60 min, the mixture was diluted with 1N aq. HCl and EtOAc. The aq. layer was extracted with EtOAc (2×). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was concentrated and then triturated with in Et2O. The resulting suspension was sonicated, then filtered. The collected solid was washed with Et2O (2×), dried under a stream of N2 (g), then dried under vacuum to give 1-(4-bromo-5-chloro-2-methoxyphenyl)-7-fluoro-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.370 g, 0.700 mmol, 100% yield) as an off white solid. m/z (ESI) 527.7 (M+H)+.

Workup

  1. extractionThe aq. layer was extracted with EtOAc (2×)
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. concentrationThe residue was concentrated
  6. customtriturated with in Et2O
  7. customThe resulting suspension was sonicated
  8. filtrationfiltered
  9. washThe collected solid was washed with Et2O (2×)
  10. dry with materialdried under a stream of N2 (g)
  11. customdried under vacuum

Sources & evidence

ORD record
ord-67c158814ce94fb288e166fc65a5b5ed
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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