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Gamma-Butyrolactone → HCID 178520695, Verbindung

HRID 45862
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 45862
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:13]3[CH:14]=[C:15]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)=[O:21])[CH:16]=[CH:17][CH:18]=3)=[N:10][NH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1.[C:33]1(=[O:38])[O:37][CH2:36][CH2:35][CH2:34]1.[Na].C[Si](C)(C)N[Si](C)(C)C>O1CCCC1>[OH:38][CH2:33][CH2:34][CH2:35][C:36]([NH:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20](=[O:21])[NH:22][C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:25][CH:24]=4)[CH:14]=3)=[N:10][NH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1)=[O:37]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7302Gamma-ButyrolactoneHCID 45051731Sodium hexamethyidisilazaneHCID 178507322HCID 178507322, Verbindung

Produkt 1

HCID 178520695HCID 178520695, VerbindungAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

30 mg (0.068 mmol) of 1-{3-[4-(2-aminopyridin-4-yl)-1H-pyrazol-3-yl]phenyl}-3-[4-(trifluoromethyl)phenyl]urea were dissolved in 2 ml of dry tetrahydrofuran and 15 μl (0.34 mmol) of γ-butyrolactone were added. The reaction mixture was cooled to 0° C. and a solution of 680 μl (0.68 mmol) of hexamethyldisilazane sodium salt 1M in THF in 2 ml of the same solvent were added dropwise. The mixture was maintained at 0° C. for 6 hours and at room temperature overnight, then partitioned between dichloromethane and water. The organic phase was dried over sodium sulphate and evaporated. The crude was finally purified by preparative HPLC in reverse phase conditions (basic eluant), giving 20 mg (59%) of the title compound.

Aufarbeitung

  1. temperatureThe mixture was maintained at 0° C. for 6 hours and at room temperature overnight
  2. custompartitioned between dichloromethane and water
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customevaporated
  5. customThe crude was finally purified by preparative HPLC in reverse phase conditions (basic eluant)

Quellen und Nachweise

ORD-Eintrag
ord-3cff4afe910941b08835c59a82d566ad
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08541575B2

Notizen zur Reaktion

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