Ammonium Chloride → HCID 117737014, compound

HRID 1504507Notes

Reaction equation

HRID 1504507 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][O:4][N:3]=1.[Br:7][C:8]1[C:9]([Cl:31])=[CH:10][C:11]([O:29][CH3:30])=[C:12]([N:14]2[C:23]3[C:18](=[CH:19][C:20]([S:24](Cl)(=[O:26])=[O:25])=[CH:21][CH:22]=3)[CH:17]=[CH:16][C:15]2=[O:28])[CH:13]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl-].[NH4+]>C1COCC1>[Br:7][C:8]1[C:9]([Cl:31])=[CH:10][C:11]([O:29][CH3:30])=[C:12]([N:14]2[C:23]3[C:18](=[CH:19][C:20]([S:24]([NH:1][C:2]4[CH:6]=[CH:5][O:4][N:3]=4)(=[O:26])=[O:25])=[CH:21][CH:22]=3)[CH:17]=[CH:16][C:15]2=[O:28])[CH:13]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 18102163-IsoxazolamineHCID 2733832Lithium HexamethyldisilazideHCID 117737271HCID 117737271, compound

Product 1

HCID 117737014HCID 117737014, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-aminoisoxazole (0.041 ml, 0.548 mmol) and 1-(5-bromo-4-chloro-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonyl chloride (0.254 g, 0.548 mmol) in THF (5.48 ml) was cooled to 0° C., at which point LiHMDS, 1.0M in THF (1.152 ml, 1.152 mmol) was added drop wise. After 40 minutes in the ice bath, the reaction was complete and ammonium chloride (sat aq) was added and the product was extracted with ethyl acetate (×3). The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was purified via MPLC, eluting with 0-100% ethyl acetate in heptane to yield 1-(5-bromo-4-chloro-2-methoxyphenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.096 g, 0.188 mmol, 34.3% yield) as a light-yellow solid. m/z (ESI) 510.0 (M+H)+.

Workup

  1. additionwas added drop wise
  2. extractionthe product was extracted with ethyl acetate (×3)
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified via MPLC
  7. washeluting with 0-100% ethyl acetate in heptane

Sources & evidence

ORD record
ord-eafd449df16b44a2aeda3a8eb5a9036c
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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