Methanol → HCID 178499252, Verbindung

HRID 2099659

Reaktionsgleichung

Reaktionsgleichung von HRID 2099659
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:19])=[CH:8][C:9]=1[NH:10][CH:11]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[O:13][CH2:12]1)=[O:4].N1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH3:26]O.C([O:31][CH2:32][CH3:33])(=O)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:19])=[CH:8][C:9]=1[N:10]([CH:11]1[CH2:16][O:15][C:14]([CH3:17])([CH3:18])[O:13][CH2:12]1)[C:32]([C@H:33]1[CH2:25][CH2:24][C@H:23]([CH3:26])[CH2:22][CH2:21]1)=[O:31])=[O:4]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 1049Pyridine3×HCID 8857Ethyl AcetateHCID 577954295-Bromo-3-(2,2-dimethyl-[1,3]dioxan-5-ylamino)-thiophene-2-carboxylic acid methyl ester

Produkt 1

HCID 178499252HCID 178499252, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel3×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a mixture of 5-bromo-3-(2,2-dimethyl-[1,3]dioxan-5-ylamino)-thiophene-2-carboxylic acid methyl ester (200 mg, 0.57 mmol) in toluene (1 mL) and pyridine (100 μl, 1.23 mmol), acid chloride in toluene prepared above (1.1 mL, 1.05 mmol) was added. The reaction mixture was refluxed for 16 h. TLC showed the presence of starting material. Pyridine (50 μl, 0.62 mmol) and acid chloride in totuene (0.5 mL, 0.47 mmol) were added and the refluxing was continued for 24 h. The mixture was cooled to 5° C. Toluene (2 mL) and pyridine (0.2 mL) were added. After stirring for 5 min MeOH (0.5 mL) was added and the mixture was stirred for 10 min. It was diluted with ethyl acetate, washed with saturated NaHCO3 and brine, dried and evaporated. The crude reaction mixture was chromatographed over silica gel (hexane-ethyl acetate mixtures as eluents) yielding 5-bromo-3-[(2,2-dimethyl-[1,3]dioxan-5-yl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (35 mg) contaminated with a small impurity. This material was used for the next step.

Aufarbeitung

  1. customprepared above (1.1 mL, 1.05 mmol)
  2. additionwas added
  3. temperatureThe reaction mixture was refluxed for 16 h
  4. additionwas added
  5. washwashed with saturated NaHCO3 and brine
  6. customdried
  7. customevaporated
  8. customThe crude reaction mixture
  9. customwas chromatographed over silica gel (hexane-ethyl acetate mixtures as eluents)

Quellen und Nachweise

ORD-Eintrag
ord-2286d706ee8f4a3c8616a93c69ca4fb8
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569600B2

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