Sodium hydride → 2-(2,3-Dihydroxy-propylamino)-4-(6,6-dimethyl-4-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-indazol-1-yl)-benzonitrile

HRID 900477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 900477
[CH3:1][C:2]1([CH3:16])[CH2:10][C:9]2[NH:8][N:7]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:5]=2[C:4](=[O:15])[CH2:3]1.[H-].[Na+].[OH:19][CH:20]([CH2:32][OH:33])[CH2:21][NH:22][C:23]1[CH:30]=[C:29](F)[CH:28]=[CH:27][C:24]=1[C:25]#[N:26].[NH4+].[Cl-]>CC(N(C)C)=O>[OH:19][CH:20]([CH2:32][OH:33])[CH2:21][NH:22][C:23]1[CH:30]=[C:29]([N:8]2[C:9]3[CH2:10][C:2]([CH3:16])([CH3:1])[CH2:3][C:4](=[O:15])[C:5]=3[C:6]([C:11]([F:14])([F:13])[F:12])=[N:7]2)[CH:28]=[CH:27][C:24]=1[C:25]#[N:26]

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 441904636,6-Dimethyl-3-(trifluoromethyl)-1,5,6,7-tetrahydro-4H-indazol-4-oneHCID 669527352-(2,3-Dihydroxy-propylamino)-4-fluorobenzonitrile

Produkt 1

HCID 669529362-(2,3-Dihydroxy-propylamino)-4-(6,6-dimethyl-4-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-indazol-1-yl)-benzonitrileAusbeute 97,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a mixture of 6,6-Dimethyl-3-trifluoromethyl-1,5,6,7-tetrahydro-indazol-4-one (0.961 g, 4.14 mmol, 1 eq) and NaH (99 mg, 4.14 mmol, 1 eq) in dimethyl acetamide (20 mL) was added slowly 2-(2,3-Dihydroxy-propylamino)-4-fluorobenzonitrile (0.87 g, 4.14 mmol, 1 eq). Then the reaction mixture was stirred at 150° C. overnight, cooled, poured into saturated NH4Cl aq. solution (100 mL), extracted by EtOAc (3×150 mL), dried over Na2SO4, filtered, concentrated. The crude product was purified by flash silica gel chromatography, eluted by EtOAc to give 2-(2,3-Dihydroxy-propylamino)-4-(6,6-dimethyl-4-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-indazol-1-yl)-benzonitrile (1.7 g, 97% yield). LCMS (m/z): M+H=423.

Aufarbeitung

  1. temperaturecooled
  2. extractionextracted by EtOAc (3×150 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash silica gel chromatography
  7. washeluted by EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-006af5b51fb84bccb025135885bf0e5c
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07358370B2

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