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 30709Notes

Reaction equation

HRID 30709 reaction equation
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

Participants

5

Reactant 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

Product 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)acrylamideYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0cda900b3fe94be79e82df43910c6caf
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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