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Acetic Acid → HCID 178453912, Verbindung

HRID 2042404
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2042404
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH:15]=O)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[N:18]1([C:24]2[C:29]3[CH:30]=[CH:31][S:32][C:28]=3[CH:27]=[CH:26][N:25]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.CC(O)=O.C([O-])(O)=O.[Na+]>ClCCCl>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][N:21]2[CH2:22][CH2:23][N:18]([C:24]3[C:29]4[CH:30]=[CH:31][S:32][C:28]=4[CH:27]=[CH:26][N:25]=3)[CH2:19][CH2:20]2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]
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Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 109660274-(Piperazin-1-yl)thieno[3,2-c]pyridineHCID 178453924HCID 178453924, Verbindung

Produkt 1

HCID 178453912HCID 178453912, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11
1,2-Dichloroethane
Lösungsmittel

Versuchsvorschrift

trans-[4-(2-oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester [CAS-Nr. 215790-29-7] (1.0 g, 4 mmol) was added to a solution under N2 of commercially available 4-piperazine-1-yl-thieno[3,2-c]pyridine [CAS-Nr. 106261-27-2] (0.85 g, 4 mmol) in 1,2-dichloroethane (45 ml) and AcOH (0.22 ml, 4 mmol). The resulting reaction mixture was stirred 8 h at room temperature before addition of Na(AcO)3BH (1.2 g, 6 mmol). Stirring was continued over night at room temperature. Sat. aq. NaHCO3 sol. was added and the product was extracted with EtOAc (2×). The combined organic layers were washed with H2O and brine. After drying (MgSO4) the solvent was evaporated and the product was purified by flash chromatography on silica gel (CH2Cl2/MeOH, 100:0 to 90:10) to yield trans-{4-[2-(4-thieno[3,2-c]pyridin-4-yl-piperazin-1-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester as a light yellow solid (1.2 g, 72%), MS (ISP) m/z=445.3 [(M+H)+].

Aufarbeitung

  1. customThe resulting reaction mixture
  2. waitwas continued over night at room temperature
  3. extractionthe product was extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with H2O and brine
  5. dry with materialAfter drying (MgSO4) the solvent
  6. customwas evaporated
  7. customthe product was purified by flash chromatography on silica gel (CH2Cl2/MeOH, 100:0 to 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-376ab6342ae54c34a29a6ea0289ab0a1
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08586579B2

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