Sodium Hydroxide → (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-(4-([(4-propyl-4H-1,2,4-triazol-3-yl)methyl]thio)phenyl)acrylamide

HRID 30709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30709
C(O[C:9]([S:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:35])/[CH:20]=[CH:21]/[C:22]2[CH:23]=[N:24][N:25]([CH3:34])[C:26]=2[C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:14][CH:13]=1)=O)C1C=CC=CC=1.ClC[C:38]1[N:42]([CH2:43][CH2:44][CH3:45])[CH:41]=[N:40][N:39]=1.[OH-].[Na+]>C(O)C>[F:33][C:30]1[CH:29]=[CH:28][C:27]([C:26]2[N:25]([CH3:34])[N:24]=[CH:23][C:22]=2/[CH:21]=[CH:20]/[C:19]([NH:18][C:15]2[CH:14]=[CH:13][C:12]([S:11][CH2:9][C:38]3[N:42]([CH2:43][CH2:44][CH3:45])[CH:41]=[N:40][N:39]=3)=[CH:17][CH:16]=2)=[O:35])=[CH:32][CH:31]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 229387563-(chloromethyl)-4-propyl-4H-1,2,4-triazoleHCID 86602524(2E)-N-{4-[(benzyloxycarbonyl)sulfanyl]phenyl}-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylamide

Produkt 1

HCID 69206966(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-(4-([(4-propyl-4H-1,2,4-triazol-3-yl)methyl]thio)phenyl)acrylamideAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of (2E)-N-{4-[(benzyloxycarbonyl)sulfanyl]phenyl}-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylamide (488 mg), 3-(chloromethyl)-4-propyl-4H-1,2,4-triazole (240 mg), a 1N aqueous sodium hydroxide solution (3 ml) and ethanol (30 ml) was stirred at room temperature for 3 hrs. The reaction mixture was concentrated, poured into water, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated to give (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-(4-{[(4-propyl-4H-1,2,4-triazol-3-yl)methyl]thio}phenyl)acrylamide (310 mg, 65%) as pale-yellow crystals.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additionpoured into water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0cda900b3fe94be79e82df43910c6caf
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423159B2

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