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 602411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602411
[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-fluoro-benzonitrile (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-765c969af6fe4d179386412ee976228c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906529B2

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