StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → ethyl 6'-(5-methyl-1H-pyrazol-4-yl)-4'-oxo-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-thieno[3,2-d]pyrimidine]-4-carboxylate

HRID 2364091
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2364091
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[N:9][NH:10][C:11]=2[CH3:12])[S:4][C:3]=1[C:13]([NH2:15])=[O:14].O=[C:17]1[CH2:22][CH2:21][CH:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]1.[O-]S([O-])(=O)=O.[Mg+2].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.C([O-])(O)=O.[Na+]>CC(N(C)C)=O>[CH3:12][C:11]1[NH:10][N:9]=[CH:8][C:7]=1[C:5]1[S:4][C:3]2[C:13](=[O:14])[NH:15][C:17]3([CH2:22][CH2:21][CH:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]3)[NH:1][C:2]=2[CH:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 24083Sulfuric acid magnesium salt (1:1)HCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 516892Sodium BicarbonateHCID 667430133-amino-5-(5-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide

Produkt 1

HCID 66744085
ethyl 6'-(5-methyl-1H-pyrazol-4-yl)-4'-oxo-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-thieno[3,2-d]pyrimidine]-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3-amino-5-(5-methyl-1H-pyrazol-4-yl) thiophene-2-carboxamide (0.111 g, 0.50 mmol), ethyl 4-oxocyclohexanecarboxylate (0.34 g, 2.00 mmol), MgSO4 (0.120 g, 1.00 mmol), CSA (0.012 g, 0.05 mmol) and DMA (3 mL) was stirred at 100° C. for 1 h. The mixture was poured into saturated aqueous NaHCO3 and extracted with EtOAc, and the extract was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, hexane to EtOAc then to 80:20 EtOAc/MeOH). The obtained residue was triturated with EtOAc, and the precipitate was collected by filtration to afford the title compound (96 mg, 51%, a mixture of 3:2 cis/trans isomers, absolute structure not determined) as yellow solid:

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialthe extract was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (Purif, silica gel, hexane to EtOAc
  6. customThe obtained residue was triturated with EtOAc
  7. filtrationthe precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-090d9da8ac454ec78cb3a85acabb34a0
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08691828B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion