N-[(4-methoxyphenyl)methyl]-1,3-thiazol-2-amine → 4-Chloro-N-(4-methoxybenzyl)-N-(thiazol-2-YL)quinoline-7-sulfonamide

HRID 1473412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1473412
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][NH:8][C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[CH:5][CH:4]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl:26][C:27]1[C:36]2[C:31](=[CH:32][C:33]([S:37](OC3C(F)=C(F)C(F)=C(F)C=3F)(=[O:39])=[O:38])=[CH:34][CH:35]=2)[N:30]=[CH:29][CH:28]=1>C1COCC1>[Cl:26][C:27]1[C:36]2[C:31](=[CH:32][C:33]([S:37]([N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:15][CH:14]=3)[C:9]3[S:10][CH:11]=[CH:12][N:13]=3)(=[O:38])=[O:39])=[CH:34][CH:35]=2)[N:30]=[CH:29][CH:28]=1

Komponenten

5

Edukt 3

HCID 578640N-[(4-methoxyphenyl)methyl]-1,3-thiazol-2-amineHCID 2733832Lithium HexamethyldisilazideHCID 86687458Perfluorophenyl 4-chloroquinoline-7-sulfonate

Produkt 1

HCID 866874604-Chloro-N-(4-methoxybenzyl)-N-(thiazol-2-YL)quinoline-7-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of N-(4-methoxybenzyl)thiazol-2-amine (0.306 g, 1.389 mmol) in THF (5.29 ml) was cooled to −78° C. for 10 minutes, and lithium bis(trimethylsilyl)amide (1.0M solution in THF) (1.323 ml, 1.323 mmol) was added drop wise. The cold bath was removed for 5 minutes, and then the reaction vessel was re-cooled to −78° C. for 10 minutes. A solution of perfluorophenyl 4-chloroquinoline-7-sulfonate (0.542 g, 1.323 mmol) in THF (2.65 ml, 1.323 mmol) was added drop wise, and the reaction was stirred for 15 minutes until complete conversion to the desired product. After warming to RT, the reaction was quenched with sat. aq ammonium chloride solution, diluted with EtOAc (5 mL) and washed with water (10 mL×2). The combined organics were dried over sodium sulfate, filtered and concentrated. The material was then purified via silica gel chromatography (40-g column) eluting with 0 to 100% ethyl acetate in heptanes, to yield 4-chloro-N-(4-methoxybenzyl)-N-(thiazol-2-yl)quinoline-7-sulfonamide (0.481 g, 1.079 mmol, 82% yield) as a white solid. m/z (ESI) 446.1 (M+H)+.

Aufarbeitung

  1. customThe cold bath was removed for 5 minutes

Quellen und Nachweise

ORD-Eintrag
ord-27a55f1269194e4ab91f183b25a3321f
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012443B2

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