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Hydrochloric Acid → 1-(5-Bromo-2-methoxy phenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide

HRID 1504439
Notes
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Reaction equation

HRID 1504439 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:34][CH3:35])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18](OC4C(F)=C(F)C(F)=C(F)C=4F)(=[O:20])=[O:19])=[CH:15][CH:16]=3)[CH:11]=[CH:10][C:9]2=[O:33])[CH:7]=1.[O:36]1[CH:40]=[CH:39][C:38]([NH2:41])=[N:37]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:34][CH3:35])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([NH:41][C:38]4[CH:39]=[CH:40][O:36][N:37]=4)(=[O:20])=[O:19])=[CH:15][CH:16]=3)[CH:11]=[CH:10][C:9]2=[O:33])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 18102163-IsoxazolamineHCID 2733832Lithium hexamethyldisilazaneHCID 117736973Perfluorophenyl 1-(5-bromo-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate

Product 1

HCID 1177371161-(5-Bromo-2-methoxy phenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamideYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a RBF was added perfluorophenyl 1-(5-bromo-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate (5.92 g, 10.27 mmol) and THF (103 ml). Isoxazol-3-amine (0.950 g, 11.36 mmol) was added, and the reaction was cooled to 0° C. Lithium bis(trimethylsilyl)amide (1.0M in THF) (21.57 ml, 21.57 mmol) was added drop wise (reaction turned from clear solution to bright yellow suspension) and the reaction was allowed to stir in the ice bath for 1 h. The reaction was warmed to RT, and 1N HCl was added. The product was extracted with EtOAc (×3), and the resulting organics were dried with MgSO4 and concentrated in vacuo. The resulting light yellow solid was triturated in diethyl ether and filtered over a fine frit, rinsing with minimal ether, to yield 1-(5-bromo-2-methoxyphenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (4.245 g, 8.91 mmol, 87% yield) as an off-white solid. MS (ESI, pos. ion) m/z: [M+1] 476.1

Workup

  1. customdrop wise (reaction turned from clear solution to bright yellow suspension)
  2. temperatureThe reaction was warmed to RT
  3. extractionThe product was extracted with EtOAc (×3)
  4. dry with materialthe resulting organics were dried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting light yellow solid was triturated in diethyl ether
  7. filtrationfiltered over a fine frit
  8. washrinsing with minimal ether

Sources & evidence

ORD record
ord-00250883797146a0b8ff191b6c08b9ec
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09212182B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes