2,2,2-Trifluoroethanesulfonyl chloride → 3-cyclopentyl-N-thiazol-2-yl-2-[4-(2,2,2-trifluoro-ethanesulfonylamino)-phenyl]-propionamide

HRID 2296953Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2296953
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[C:9]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[O:10])=[CH:4][CH:3]=1.[F:23][C:24]([F:31])([F:30])[CH2:25][S:26](Cl)(=[O:28])=[O:27]>N1C=CC=CC=1>[CH:18]1([CH2:17][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][S:26]([CH2:25][C:24]([F:31])([F:30])[F:23])(=[O:28])=[O:27])=[CH:7][CH:6]=2)[C:9]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[O:10])[CH2:22][CH2:21][CH2:20][CH2:19]1

Komponenten

4

Edukt 2

HCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 99488022-(4-amino-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide

Produkt 1

HCID 102764103-cyclopentyl-N-thiazol-2-yl-2-[4-(2,2,2-trifluoro-ethanesulfonylamino)-phenyl]-propionamideAusbeute 42,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of 2-(4-amino-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide (prepared in Example 3, 158 mg, 0.5 mmol) in pyridine (5 mL) at 25° C. was treated with 2,2,2-trifluoroethanesulfonyl chloride (63.5 μL, 0.57 mmol). The reaction was stirred at 25° C. for 48 h and was then concentrated in vacuo. High pressure liquid chromatography (Chromegasphere SI-60, 10 μM, 60 Å, 25 cm×23 cm ID, 40/60 heptane/ethyl acetate) afforded the 3-cyclopentyl-N-thiazol-2-yl-2-[4-(2,2,2-trifluoro-ethanesulfonylamino)-phenyl]-propionamide (98.1 mg, 42.4%) as a light yellow oil: EI-HRMS m/e calcd for C19H22F3N3O3S2 (M+) 461.1054, found 461.1064.

Aufarbeitung

  1. concentrationwas then concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4ce0032dfcb840b4bd0b920dd4584973
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06489485B2

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