Diisopropylethylamine → 2-(3-Benzyloxy-phenyl)-5-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-2H-pyrazol-3-ylamine

HRID 2282732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2282732
[C:1]([Si:5]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[O:6][CH2:7][C:8]([CH3:15])([CH3:14])[C:9](=O)[CH2:10][C:11]#[N:12])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:29]([O:36][C:37]1[CH:38]=[C:39]([NH:43][NH2:44])[CH:40]=[CH:41][CH:42]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CCN(C(C)C)C(C)C>C(O)C.CCOC(C)=O>[CH2:29]([O:36][C:37]1[CH:38]=[C:39]([N:43]2[C:11]([NH2:12])=[CH:10][C:9]([C:8]([CH3:15])([CH3:14])[CH2:7][O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:44]2)[CH:40]=[CH:41][CH:42]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 12891839(3-(Benzyloxy)phenyl)hydrazine hydrochlorideHCID 866872835-(tert-Butyl-diphenyl-silanyloxy)-4,4-dimethyl-3-oxo-pentanenitrile

Produkt 1

HCID 866872842-(3-Benzyloxy-phenyl)-5-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-2H-pyrazol-3-ylamineAusbeute 107 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of Intermediate 153b (1.00 g, 2.63 mmol) in ethanol (IMS grade, 20 mL) was treated with 3-benzyloxyphenylhydrazine hydrochloride (0.66 mL, 2.63 mmol) then DIPEA (0.46 mL, 2.63 mmol) and the mixture was heated to reflux for 114 h. The cooled reaction mixture was diluted with EtOAc and a saturated aqueous sodium bicarbonate solution and the mixture was filtered and the phases separated. The aqueous layer was extracted with EtOAc (×2) and the combined organic phase was washed with brine, dried (Na2SO4), and concentrated in vacuo to give an orange oil (1.62 g). The gum was purified by FCC, using 0-20% EtOAc in cyclohexane, to give the title compound as a yellow oil (1.21 g, 80%). LCMS (Method 3): Rt 5.40 min, m/z 576.5 [MH+].

Aufarbeitung

  1. temperatureto reflux for 114 h
  2. customThe cooled reaction mixture
  3. filtrationa saturated aqueous sodium bicarbonate solution and the mixture was filtered
  4. customthe phases separated
  5. extractionThe aqueous layer was extracted with EtOAc (×2)
  6. washthe combined organic phase was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-296a9a153248492a8a4cc25733ca7eaf
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139584B2

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