2-Thiopheneacetyl chloride → (Z)-N-[2,3-Dihydro-4-(6-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-5-yl]-2-thiopheneacetamide

HRID 382067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 382067
[NH2:1][C:2]1[C:3]([C:20]2[CH:28]=[C:27]3[C:23]([CH:24]=[CH:25][NH:26]3)=[CH:22][CH:21]=2)=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:12]\[C:13]1[NH:14][CH:15]=[CH:16][C:17]=1[O:18][CH3:19].[S:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[CH2:34][C:35](Cl)=[O:36].C(=O)(O)[O-].[Na+]>O1CCCC1.O>[NH:26]1[C:27]2[C:23](=[CH:22][CH:21]=[C:20]([C:3]3[C:2]([NH:1][C:35](=[O:36])[CH2:34][C:30]4[S:29][CH:33]=[CH:32][CH:31]=4)=[CH:10][CH:9]=[C:8]4[C:4]=3/[C:5](=[CH:12]/[C:13]3[NH:14][CH:15]=[CH:16][C:17]=3[O:18][CH3:19])/[C:6](=[O:11])[NH:7]4)[CH:28]=2)[CH:24]=[CH:25]1

Komponenten

6

Edukt 3

HCID 1623622-Thiopheneacetyl chlorideHCID 516892Sodium BicarbonateHCID 18363862(Z)-5-amino-1,3-dihydro-4-(6-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

Produkt 1

HCID 9913671(Z)-N-[2,3-Dihydro-4-(6-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-5-yl]-2-thiopheneacetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (Z)-5-amino-1,3-dihydro-4-(6-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (22 mg, 0.059 mmol) (from Step B above) in 2 mL tetrahydrofuran was added 2-thiopheneacetyl chloride (20 mg, 0.12 mmol) (Aldrich) and a saturated aqueous solution of sodium bicarbonate (0.15 mL). The reaction was stirred at room temperature for 16 hours at which time the reaction was diluted with water (10 mL), and the THF was evaporated in vacuo. The product was then extracted with EtOAc, and the combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The resulting powder was recrystallized from EtOAc/Hex to give product as yellow crystals. (Yield 19 mg, 66%).

Aufarbeitung

  1. customthe THF was evaporated in vacuo
  2. extractionThe product was then extracted with EtOAc
  3. dry with materialthe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting powder was recrystallized from EtOAc/Hex
  6. customto give product as yellow crystals

Quellen und Nachweise

ORD-Eintrag
ord-f72c4870e2ba4c2ba00fdf019d4101a5
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06307056B1

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