Methanol → N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-(hydroxymethyl)-1H-1,2,3-triazole-4-carboxamide

HRID 1717317Notes

Reaction equation

HRID 1717317 reaction equation
C([O:8][CH2:9][C:10]1[N:14]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([NH:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=2)[N:13]=[N:12][C:11]=1[C:26]([NH:28][CH:29]1[CH2:31][CH2:30]1)=[O:27])C1C=CC=CC=1.CO>CN(C=O)C.[C].[Pd]>[CH:29]1([NH:28][C:26]([C:11]2[N:12]=[N:13][N:14]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([NH:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=3)[C:10]=2[CH2:9][OH:8])=[O:27])[CH2:30][CH2:31]1

Participants

5

Reactant 2

HCID 887MethanolHCID 576647725-[(benzyloxy)methyl]-N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 57665224N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-(hydroxymethyl)-1H-1,2,3-triazole-4-carboxamideYield 76%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[(benzyloxy)methyl]-N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide (4.29 g) obtained in Example 94 in DMF (60 ml)-methanol (180 ml) was added palladium-carbon (1.0 g). 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 (hexane/ethyl acetate=1/1 to ethyl acetate/methanol=4/1). The resultant product was recrystallized from ethyl acetate/hexane to give the title compound as a colorless powder (2.56 g, 76%).

Workup

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

Sources & evidence

ORD record
ord-cd2f95082851435883ad6281f86605ae
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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