2-Aminothiazole → (2E)-2-(3-chloro-4-methylsulfonylphenyl)-2-cyclopentyloxyimino-N-(1,3-thiazol-2-yl)acetamide

HRID 600948Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600948
[Cl:1][C:2]1[CH:3]=[C:4](/[C:12](=[N:16]\[O:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)/[C:13]([OH:15])=O)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[S:23]1[CH:27]=[CH:26][N:25]=[C:24]1[NH2:28].C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4](/[C:12](=[N:16]\[O:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)/[C:13]([NH:28][C:24]2[S:23][CH:27]=[CH:26][N:25]=2)=[O:15])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

Komponenten

5

Edukt 3

HCID 21552-AminothiazoleHCID 81531DiisopropylethylamineHCID 87416741HCID 87416741, Verbindung

Produkt 1

HCID 24990017(2E)-2-(3-chloro-4-methylsulfonylphenyl)-2-cyclopentyloxyimino-N-(1,3-thiazol-2-yl)acetamideAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

(E)-(3-Chloro-4-methanesulfonyl-phenyl)-cyclopentyloxyimino-acetic acid (prepared as in Example 1, 93 mg, 0.27 mmol), thiazol-2-ylamine (27 mg, 0.27 mmol) and N,N-diisopropylethylamine (141 μL, 0.82 mmol) were combined in acetonitrile (1.25 mL) and cooled in an ice bath. O-(7-Azabenzotriazole-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate (103 mg, 0.27 mmol) was added and the ice bath was removed. After stirring 2 h, the reaction mixture was evaporated in vacuo. The residue was treated with saturated aqueous sodium bicarbonate solution (1 mL) and extracted with chloroform (2×3 mL). The combined organic phases were dried over sodium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (Merck silica gel 60, 40-63 μm; 60% ethyl acetate/hexanes) to afford (E)-2-(3-chloro-4-methanesulfonyl-phenyl)-2-cyclopentyloxyimino-N-thiazol-2-yl-acetamide (71 mg, 62%) as a white solid after lyophilization from aqueous acetonitrile: LC-MS (ESI) m/e calcd for C17H18ClN3O4S2 [M+] 427.04, found 428 [M+H+]; H1-NMR (400 MHz, CDCl3) δ ppm 1.68 (m, 4 H, 2×CH2), 1.90 (m, 4 H, 2×CH2), 3.32 (s, 3 H, SO2CH3), 4.96 (m, 1 H, OCH), 7.05 (d, J=3.5 Hz, 1 H, Ar), 7.52 (d, J=3.5 Hz, 1 H, Ar), 7.60 (dd, Jo=8.2, Jm=1.2 Hz, 1 H, Ar), 7.71 (d, Jm=1.2 Hz, 1 H, Ar), 8.20 (d, Jo=8.2 Hz, 1 H, Ar), 10.20 (s, 1 H, NH).

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. customthe ice bath was removed
  3. customthe reaction mixture was evaporated in vacuo
  4. additionThe residue was treated with saturated aqueous sodium bicarbonate solution (1 mL)
  5. extractionextracted with chloroform (2×3 mL)
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by flash column chromatography (Merck silica gel 60, 40-63 μm; 60% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-01a9a328e6dd4eeba0015c6b2b3ce204
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902248B2

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