4-(Trifluoromethyl)phenyl isocyanate → 1-(3-{1-(4-methoxybenzyl)-4-[2-(methylamino)pyridin-4-yl]-1H-pyrazol-3-yl}phenyl)-3-[4-(trifluoromethyl)phenyl]urea

HRID 45866

Reaktionsgleichung

Reaktionsgleichung von HRID 45866
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH3:20])[CH:14]=3)=[CH:11][N:10]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[F:30][C:31]([F:42])([F:41])[C:32]1[CH:37]=[CH:36][C:35]([N:38]=[C:39]=[O:40])=[CH:34][CH:33]=1.[Na]>CN(C)C=O>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:10]2[CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH3:20])[CH:14]=3)[C:8]([C:4]3[CH:3]=[C:2]([NH:1][C:39]([NH:38][C:35]4[CH:34]=[CH:33][C:32]([C:31]([F:30])([F:41])[F:42])=[CH:37][CH:36]=4)=[O:40])[CH:7]=[CH:6][CH:5]=3)=[N:9]2)=[CH:27][CH:26]=1

Komponenten

5

Edukt 3

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 5360545SodiumHCID 671862484-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-N-methylpyridin-2-amine

Produkt 1

HCID 671843231-(3-{1-(4-methoxybenzyl)-4-[2-(methylamino)pyridin-4-yl]-1H-pyrazol-3-yl}phenyl)-3-[4-(trifluoromethyl)phenyl]ureaAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

250 mg (0.65 mmol) of 4-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-N-methylpyridin-2-amine were dissolved in 10 ml of dry dimethylformamide and 92 μl of p-trifluoromethyl-phenylisocyanate were added. The reaction was stirred at room temperature overnight, poured into aqueous sodium hydrogenocarbonate and extracted with dichloromethane. The organic phase was then dried over sodium sulphate and evaporated. The residue was purified by flash-chromatography on a silica gel column CH2C12-CH3COCH3; from 9/1 to 8/2), giving 234 mg (63%) of the title compound.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase was then dried over sodium sulphate
  3. customevaporated
  4. customThe residue was purified by flash-chromatography on a silica gel column CH2C12-CH3COCH3

Quellen und Nachweise

ORD-Eintrag
ord-156ace3574a8420d9fecbb93f87a9ee7
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541575B2

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