Sodium Hydroxide → N-{3-Cyano-4-[4-(N-(2-hydroxyethyl)amino)piperidin-1-yl]phenyl}-1-(4-trifluoromethylphenyl)-5-methylpyrazole-4-carboxamide

HRID 1744626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1744626
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH3:14])=[C:12]([C:15]([OH:17])=O)[CH:11]=[N:10]2)=[CH:5][CH:4]=1.[NH2:20][C:21]1[CH:22]=[CH:23][C:24]([N:29]2[CH2:34][CH2:33][CH:32]([N:35]([CH2:43][CH2:44][OH:45])C(OC(C)(C)C)=O)[CH2:31][CH2:30]2)=[C:25]([CH:28]=1)[C:26]#[N:27].[OH-].[Na+]>FC(F)(F)C(O)=O>[C:26]([C:25]1[CH:28]=[C:21]([NH:20][C:15]([C:12]2[CH:11]=[N:10][N:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:18])=[CH:8][CH:7]=3)[C:13]=2[CH3:14])=[O:17])[CH:22]=[CH:23][C:24]=1[N:29]1[CH2:30][CH2:31][CH:32]([NH:35][CH2:43][CH2:44][OH:45])[CH2:33][CH2:34]1)#[N:27]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 107784295-methyl-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-4-carboxylic acidHCID 222280265-amino-2-[4-(N-tert-butoxycarbonyl-2-hydroxyethylamino)piperidin-1-yl]benzonitrile

Produkt 1

HCID 22228210N-{3-Cyano-4-[4-(N-(2-hydroxyethyl)amino)piperidin-1-yl]phenyl}-1-(4-trifluoromethylphenyl)-5-methylpyrazole-4-carboxamideAusbeute 9,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

The reaction and treatment in the same manner as in Example 64 were conducted using 1-(4-trifluoromethylphenyl)-5-methylpyrazole-4-carboxylic acid (1.94 g) and 5-amino-2-[4-(N-tert-butoxycarbonyl-2-hydroxyethylamino)piperidin-1-yl]benzonitrile (2.59 g) and the resulting mixture was further stirred in trifluoroacetic acid (10 ml) under ice-cooling for 1 h. The reaction mixture was treated with aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was recrystallized from a mixed solvent of dimethylformamide-water to give the title compound (0.34 g), melting point: 202° C.

Aufarbeitung

  1. customThe reaction and treatment in the same manner as in Example 64
  2. temperaturecooling for 1 h
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was recrystallized from a mixed solvent of dimethylformamide-water

Quellen und Nachweise

ORD-Eintrag
ord-9eeb5718510a45458bb1e8b1e7a62836
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07015218B1

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