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Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 7-bromo-2-methyl-6-(1H-pyrazol-4-yl)-2-(2,2,2-trifluoroethyl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

HRID 2364048
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2364048
[NH2:1][C:2]1[C:6]([Br:7])=[C:5]([C:8]2[CH:9]=[N:10][NH:11][CH:12]=2)[S:4][C:3]=1[C:13]([NH2:15])=[O:14].[F:16][C:17]([F:23])([F:22])[CH2:18][C:19](=O)[CH3:20].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.[O-]S([O-])(=O)=O.[Mg+2].C([O-])(O)=O.[Na+]>CC(N(C)C)=O>[Br:7][C:6]1[C:2]2[NH:1][C:19]([CH3:20])([CH2:18][C:17]([F:23])([F:22])[F:16])[NH:15][C:13](=[O:14])[C:3]=2[S:4][C:5]=1[C:8]1[CH:9]=[N:10][NH:11][CH:12]=1
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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 516892Sodium BicarbonateHCID 5390014,4,4-Trifluorobutan-2-oneHCID 667431873-amino-4-bromo-5-(1H-pyrazol-4-yl)thiophene-2-carboxamide

Produkt 1

HCID 66744070
7-bromo-2-methyl-6-(1H-pyrazol-4-yl)-2-(2,2,2-trifluoroethyl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one
Ausbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A mixture of 3-amino-4-bromo-5-(1H-pyrazol-4-yl)thiophene-2-carboxamide (90 mg, 0.313 mmol), 4,4,4-trifluorobutan-2-one (395 mg, 3.13 mmol), CSA (7.28 mg, 0.031 mmol), MgSO4 (37.7 mg, 0.313 mmol) and DMA (2 mL) was microwave-irradiated at 150° C. for 3 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, 95:5 hexane/EtOAc to EtOAc). The obtained solid was triturated with EtOAc, and the precipitate was collected by filtration to afford the title compound (29.2 mg, 24%) as a white solid:

Aufarbeitung

  1. customwas microwave-irradiated at 150° C. for 3 h
  2. extractionextracted with EtOAc
  3. dry with materialthe extract was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to EtOAc)
  7. customThe obtained solid was triturated with EtOAc
  8. filtrationthe precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-059b5d5a60784be2a8789d71554fd99a
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08691828B2

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