Trifluoroacetic acid → N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-{[(1H-imidazol-2-ylmethyl)amino]methyl}-1H-1,2,3-triazole-4-carboxamide

HRID 1717409Notes

Reaction equation

HRID 1717409 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([NH:11][C:12]([C:14]2[N:15]=[N:16][N:17]([C:46]3[CH:51]=[CH:50][C:49]([C:52]([NH:54][CH2:55][CH3:56])=[O:53])=[CH:48][CH:47]=3)[C:18]=2[CH2:19][NH:20][CH2:21][C:22]2[N:23](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:24]=[CH:25][N:26]=2)=[O:13])[CH2:10][CH2:9]1>>[CH:8]1([NH:11][C:12]([C:14]2[N:15]=[N:16][N:17]([C:46]3[CH:47]=[CH:48][C:49]([C:52]([NH:54][CH2:55][CH3:56])=[O:53])=[CH:50][CH:51]=3)[C:18]=2[CH2:19][NH:20][CH2:21][C:22]2[NH:26][CH:25]=[CH:24][N:23]=2)=[O:13])[CH2:9][CH2:10]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57664825N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-({[(1-trityl-1H-imidazol-2-yl)methyl]amino}methyl)-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 57664919N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-{[(1H-imidazol-2-ylmethyl)amino]methyl}-1H-1,2,3-triazole-4-carboxamideYield 61.2%

Procedure

Trifluoroacetic acid (0.5 ml) was added to N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-({[(1-trityl-1H-imidazol-2-yl)methyl]amino}methyl)-1H-1,2,3-triazole-4-carboxamide (78 mg, 0.12 mmol) obtained in Example 1198, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, water (2 ml) was added to the residue, and precipitated crystals were filtered off. The filtrate was neutralized with 1N aqueous sodium hydroxide solution and concentrated to dryness. The residue was purified by silica gel column (hexane/ethyl acetate=1/1 to ethyl acetate/methanol=4/1) to give the title compound as a colorless powder (30 mg, 61%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater (2 ml) was added to the residue
  3. customprecipitated crystals
  4. filtrationwere filtered off
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by silica gel column (hexane/ethyl acetate=1/1 to ethyl acetate/methanol=4/1)

Sources & evidence

ORD record
ord-b7c1657b78c64a5089ae742c45f6b93f
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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