Diisopropylethylamine → HCID 24990020, Verbindung

HRID 600969Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600969
[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].C(N(CC)C(C)C)(C)C.[NH2:32][C:33]1[S:34][C:35]([C:38]([NH2:40])=[O:39])=[CH:36][N:37]=1>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:32][C:33]2[S:34][C:35]([C:38]([NH2:40])=[O:39])=[CH:36][N:37]=2)=[O:15])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 162272132-Amino-1,3-thiazole-5-carboxamideHCID 87416741HCID 87416741, Verbindung

Produkt 1

HCID 24990020HCID 24990020, VerbindungAusbeute 12,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(E)-(3-Chloro-4-methanesulfonyl-phenyl)-cyclopentyloxyimino-acetic acid (prepared as in Example 1, 96 mg, 0.28 mmol), N,N-diisopropylethylamine (145 μL, 0.83 mmol) and 2-amino-thiazole-5-carboxylic acid amide (prepared as in Example 12, 48 mg, 0.34 mmol) were combined in acetonitrile (1.4 mL) and cooled to 0° C. O-(7-Azabenzotriazole-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate (106 mg, 0.28 mmol) was added and the cooling bath was removed. After stirring 16 h, the reaction mixture was treated with saturated aqueous sodium bicarbonate solution (30 mL) and extracted with 10% methanol/chloroform (3×35 mL). The combined organic phases were dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (Merck silica gel 60, 40-63 μm; 2% methanol/chloroform) to afford (E)-2-[2-(3-chloro-4-methanesulfonyl-phenyl)-2-cyclopentyloxyimino-acetylamino]-thiazole-5-carboxylic acid amide (16 mg, 12%) as a white solid after lyophilization from aqueous dioxane: LC-MS (ESI) m/e calcd for C18H19ClN4O5S2 [M+] 470.05, found 471 [M+H+]: H1-NMR (400 MHz, CD3OD) δ ppm 1.66 (m, 4 H, 2×CH2), 1.92 (m, 4 H, 2×CH2), 3.34 (s, 3 H, SO2CH3), 5.04 (m, 1 H, OCH), 7.66 (dd, Jo=8.2, Jm=1.6 Hz, 1 H, Ar), 7.78 (d, Jm=1.6 Hz, 1 H, Ar), 8.05 (s, 1H, Ar), 8.17 (d, Jo=8.2 Hz, 1 H, Ar).

Aufarbeitung

  1. customthe cooling bath was removed
  2. additionthe reaction mixture was treated with saturated aqueous sodium bicarbonate solution (30 mL)
  3. extractionextracted with 10% methanol/chloroform (3×35 mL)
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by flash column chromatography (Merck silica gel 60, 40-63 μm; 2% methanol/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-fdc30729bd4f428abee138b6199de3ca
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902248B2

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