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Acetic Anhydride → n-(1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethyl)acetamide

HRID 404871
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Reaktionsgleichung von HRID 404871
[CH:1]([O:4][C:5]1[CH:34]=[CH:33][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[S:19][C:18]([CH:20]([N:22]4C(=O)C5[C:24](=CC=CC=5)[C:23]4=[O:32])[CH3:21])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].O.NN.C(N(CC)CC)C.C(OC(=O)C)(=O)C>ClCCl.CCCCCC.C(OCC)(=O)C.CO.C(O)C>[CH:1]([O:4][C:5]1[CH:34]=[CH:33][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[S:19][C:18]([CH:20]([NH:22][C:23](=[O:32])[CH3:24])[CH3:21])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]
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Komponenten

10

Edukt 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 694391172-(1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethyl)-1h-isoindole-1,3(2h)-dione

Produkt 1

HCID 23648576n-(1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethyl)acetamideAusbeute 24,2 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of Example 3C (200 mg, 0.41 mmol) at room temperature in dichloromethane (5 mL) was added hydrazine hydrate (197 uL, 4.1 mmol). Ethanol was added until a clear, single phase was formed. After an hour at room temperature, the solvent was removed under vacuum and the reaction mixture was thoroughly dried. To the resulting mixture was added dichloromethane (5 mL), triethylamine (300 uL, 2.15 mmol) and acetic anhydride (150 uL, 1.59 mmol). After two hours at room temperature, methanol was added and the solution was stirred for additional hour. The mixture was concentrated and the product was isolated via silica column chromatography (using a gradient of 25 to 75% ethyl acetate in hexane) and yielded 40 mg of the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.16-7.23 (m, 3H) 6.83-6.95 (m, 4H) 5.66 (d, J=8.09 Hz, 1H) 5.25-5.43 (m, 1H) 4.52 (heptet, J=6.25 Hz, 1H) 2.00 (s, 3H) 1.57 (d, J=6.99 3 H) 1.35 (d, J=6.25 Hz, 6H), MS (DCI): m/z 403 (M+H).

Aufarbeitung

  1. customwas formed
  2. waitAfter an hour at room temperature
  3. customthe solvent was removed under vacuum
  4. customthe reaction mixture was thoroughly dried
  5. concentrationThe mixture was concentrated
  6. customthe product was isolated via silica column chromatography (

Quellen und Nachweise

ORD-Eintrag
ord-e4623637a0c54002b39fb3769ff31b34
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08748627B2

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