Pyridine → HCID 178499328, Verbindung

HRID 1675544

Reaktionsgleichung

Reaktionsgleichung von HRID 1675544
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:22]#[C:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:8][C:9]=1[NH:10][CH:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH:21]=[CH:20][N:19]=[N:18]2)[CH2:13][CH2:12]1)=[O:4].[CH3:28][C@H:29]1[CH2:34][CH2:33][C@H:32]([C:35](Cl)=[O:36])[CH2:31][CH2:30]1.N1C=CC=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:22]#[C:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:8][C:9]=1[N:10]([C:35]([C@H:32]1[CH2:33][CH2:34][C@H:29]([CH3:28])[CH2:30][CH2:31]1)=[O:36])[CH:11]1[CH2:12][CH2:13][CH:14]([N:17]2[CH:21]=[CH:20][N:19]=[N:18]2)[CH2:15][CH2:16]1)=[O:4]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 249889805-(3,3-Dimethyl-but-1-ynyl)-3-(4-[1,2,3]triazol-1-yl-cyclohexylamino)-thiophene-2-carboxylic acid methyl esterHCID 178461265HCID 178461265, Verbindung

Produkt 1

HCID 178499328HCID 178499328, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

To a solution of 5-(3,3-dimethyl-but-1-ynyl)-3-(4-[1,2,3]triazol-1-yl-cyclohexylamino)-thiophene-2-carboxylic acid methyl ester (0.20 g, 0.50 mmol) in toluene (1 ml) is added a solution of trans-4-methylcyclohexyl carboxylic acid chloride 1 M (1.0 ml, 1.0 mmol) and pyridine (0.046 ml, 0.58 mmol). The mixture is stirred overnight at 105° C. and diluted with ethyl acetate. The organic layer is washed with NaHCO3 sat (2×) and brine. The organic layer is dried with sodium sulfate, filtered and concentrated under reduce pressure. The residue is purified by silica gel column chromatography (20% ethyl acetate/hexane to 100% ethyl acetate followed by 10% MeOH/ethyl acetate) to give 5-(3,3-dimethyl-but-1-ynyl)-3-[(trans-4-methyl-cyclohexanecarbonyl)-(4-[1,2,3]triazol-1-yl-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl ester.

Aufarbeitung

  1. washThe organic layer is washed with NaHCO3
  2. dry with materialThe organic layer is dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel column chromatography (20% ethyl acetate/hexane to 100% ethyl acetate followed by 10% MeOH/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e0389242d9a1420fbf3a4a14faba5a8d
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003685B2

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