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Triethylamine → N-[4-(3-cyclohexyl-1-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-3-methoxyphenyl]-N-(methylsulfonyl)methanesulfonamide

HRID 915957
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 915957
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:24])[C:11]3[C:16]([CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)=[N:15][N:14]([CH3:23])[C:12]=3[N:13]=2)=[C:4]([O:25][CH3:26])[CH:3]=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>O1CCCC1>[CH:17]1([C:16]2[C:11]3[C:10](=[O:24])[NH:9][C:8]([C:5]4[CH:6]=[CH:7][C:2]([N:1]([S:28]([CH3:27])(=[O:30])=[O:29])[S:28]([CH3:27])(=[O:30])=[O:29])=[CH:3][C:4]=4[O:25][CH3:26])=[N:13][C:12]=3[N:14]([CH3:23])[N:15]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 516892Sodium BicarbonateHCID 1359488876-(4-Amino-2-methoxyphenyl)-3-cyclohexyl-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Produkt 1

HCID 136005960N-[4-(3-cyclohexyl-1-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-3-methoxyphenyl]-N-(methylsulfonyl)methanesulfonamide
Ausbeute 76,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a 6 ml tetrahydrofuran solution of 114 mg (0.323 mmol) of the compound obtained in Example 44, 49 μl (0.63 mmol) of methanesulfonyl chloride and 90 μl (0.65 mmol) of triethylamine were added, and the mixture was stirred at room temperature for 1 hour. Then, 23 μl (0.3 mmol) of methanesulfonyl chloride was further added to the reaction mixture, and the mixture was stirred at room temperature for 1 hour. Then, an aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. After the washed layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=30/1) to obtain 123 mg (75%) of the captioned compound.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with water
  4. dry with materialAfter the washed layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=30/1)

Quellen und Nachweise

ORD-Eintrag
ord-b0009f8c48d341db8e88cc6b45071178
Quelldatensatz
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07268128B2

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