Dichloromethane → HCID 117736955, compound

HRID 1504561Notes

Reaction equation

HRID 1504561 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18](Cl)(=[O:20])=[O:19])=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]2=[O:22])=[C:4]([O:23][CH3:24])[CH:3]=1.C(Cl)Cl.[NH2:28][C:29]1[CH:33]=[CH:32][O:31][N:30]=1>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([NH:28][C:29]4[CH:33]=[CH:32][O:31][N:30]=4)(=[O:20])=[O:19])=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]2=[O:22])=[C:4]([O:23][CH3:24])[CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 18102163-IsoxazolamineHCID 117737000HCID 117737000, compound

Product 1

HCID 117736955HCID 117736955, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A RBF was charged with 1-(4-bromo-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoxaline-6-sulfonyl chloride (0.800 g, 1.862 mmol), DCM (3.12 ml), and 3-aminoisoxazole (0.206 ml, 2.79 mmol) to give a thick suspension. Pyridine (6.21 ml) was added relatively quickly, leading to thinner suspension. After 2 h, the mixture was concentrated in vacuo. The residue was partitioned between EtOAc and 2N aq. HCl. The layers were separated, and the aq. layer was extracted with EtOAc (2×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (50-g SNAP Ultra column, 0-50% 3:1 EtOAc/EtOH in heptane with 10% DCM) to give 1-(4-bromo-2-methoxyphenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoxaline-6-sulfonamide (0.751 g, 1.573 mmol, 85% yield) as a white foam. m/z (ESI) 478.9 (M+H)+.

Workup

  1. customto give a thick suspension
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was partitioned between EtOAc and 2N aq. HCl
  4. customThe layers were separated
  5. extractionthe aq. layer was extracted with EtOAc (2×)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography on silica gel (50-g SNAP Ultra column, 0-50% 3:1 EtOAc/EtOH in heptane with 10% DCM)

Sources & evidence

ORD record
ord-fb69c95c27154de0b3f2af7ee1980462
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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