HCID 57664715, compound → HCID 57665121, compound

HRID 1717394Notes

Reaction equation

HRID 1717394 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([NH:32][CH2:33][CH3:34])=[O:31])=[CH:26][CH:25]=3)[C:11]=2/[CH:12]=[CH:13]/[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[O:6])[CH2:3][CH2:2]1>C(O)(=O)C.C(O)C.[C].[Pd]>[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:24]3[CH:25]=[CH:26][C:27]([C:30]([NH:32][CH2:33][CH3:34])=[O:31])=[CH:28][CH:29]=3)[C:11]=2[CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([S:20]([CH3:23])(=[O:21])=[O:22])=[CH:18][CH:19]=2)=[O:6])[CH2:2][CH2:3]1

Participants

5

Reactant 1

HCID 57664715HCID 57664715, compound

Product 1

HCID 57665121HCID 57665121, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-{(E)-2-[4-(methylsulfonyl)phenyl]vinyl}-1H-1,2,3-triazole-4-carboxamide (230 mg, 0.48 mmol) obtained in Example 401 in acetic acid (12 ml) and ethanol (4.0 ml) was added palladium-carbon (25 mg). The reaction mixture was stirred under a hydrogen atmosphere at room temperature for 5 days, and the insoluble material was filtered off. The solvent was evaporated, and the residue was purified by silica gel column (ethyl acetate/methanol=20/1 to 10/1). The resultant product was recrystallized from ethyl acetate/hexane to give the title compound as a colorless powder (150 mg, 65%).

Workup

  1. filtrationthe insoluble material was filtered off
  2. customThe solvent was evaporated
  3. customthe residue was purified by silica gel column (ethyl acetate/methanol=20/1 to 10/1)
  4. customThe resultant product was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-affa705a72074408b7ed510454fb32a1
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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