N-(2,4-dimethoxybenzyl)-1,2,4-thiadiazol-5-amine → 4-chloro-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)quinoline-7-sulfonamide

HRID 1473516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1473516
[CH3:1][O:2][C:3]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:4]=1[CH2:5][NH:6][C:7]1[S:11][N:10]=[CH:9][N:8]=1.[Cl:18][C:19]1[C:28]2[C:23](=[CH:24][C:25]([S:29](OC3C(F)=C(F)C(F)=C(F)C=3F)(=[O:31])=[O:30])=[CH:26][CH:27]=2)[N:22]=[CH:21][CH:20]=1>C1COCC1.[Cl-].[NH4+].O.CCOC(C)=O.CCCCCCC>[Cl:18][C:19]1[C:28]2[C:23](=[CH:24][C:25]([S:29]([N:6]([CH2:5][C:4]3[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:3]=3[O:2][CH3:1])[C:7]3[S:11][N:10]=[CH:9][N:8]=3)(=[O:30])=[O:31])=[CH:26][CH:27]=2)[N:22]=[CH:21][CH:20]=1

Komponenten

8

Edukt 2

HCID 57732216N-(2,4-dimethoxybenzyl)-1,2,4-thiadiazol-5-amineHCID 86687458Perfluorophenyl 4-chloroquinoline-7-sulfonate

Produkt 1

HCID 866875714-chloro-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)quinoline-7-sulfonamideAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 8900HeptaneLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

A flask was charged with N-(2,4-dimethoxybenzyl)-1,2,4-thiadiazol-5-amine (302 mg, 1.204 mmol) and THF (5471 μl) to give a clear solution. The flask was cooled in a dry ice-acetone bath for 5 min, and then a solution of perfluorophenyl 4-chloroquinoline-7-sulfonate (448.3 mg, 1.094 mmol) in THF (1 mL with a 0.5 mL syringe wash) was added drop wise. After 1 h, the mixture was diluted with saturated aq. ammonium chloride, water, and EtOAc, and the layers were separated. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (40-g Redi-Sep Gold column, 20-70% EtOAc/Heptane) to give an off-white solid. The solid was taken up in heptane and filtered. The collected solid was washed with heptane (2×), then dried under a stream of N2 (g) for 2 h to give 4-chloro-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)quinoline-7-sulfonamide (426 mg, 0.893 mmol, 82% yield) as a white solid. m/z (ESI) 477.0 (M+H)+.

Aufarbeitung

  1. customto give a clear solution
  2. temperatureThe flask was cooled in a dry ice-acetone bath for 5 min
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (40-g Redi-Sep Gold column, 20-70% EtOAc/Heptane)
  8. customto give an off-white solid
  9. filtrationfiltered
  10. washThe collected solid was washed with heptane (2×)
  11. dry with materialdried under a stream of N2 (g) for 2 h

Quellen und Nachweise

ORD-Eintrag
ord-fefeabc659fa45ee963eec79e3077c8d
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012443B2

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