Water → HCID 57664946, compound

HRID 1717402Notes

Reaction equation

HRID 1717402 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)=[C:15]([C:26]([NH:28][CH2:29][CH2:30][OH:31])=[O:27])[N:14]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[C:32](Cl)(=[O:36])[O:33][CH2:34][CH3:35].N1C=CC=CC=1.O>C1COCC1>[C:32](=[O:36])([O:33][CH2:34][CH3:35])[O:31][CH2:30][CH2:29][NH:28][C:26]([C:15]1[N:14]=[N:13][N:12]([C:9]2[CH:8]=[CH:7][C:6]([C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[CH:11][CH:10]=2)[C:16]=1[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1)=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 10928Ethyl chloroformateHCID 57665008HCID 57665008, compound

Product 1

HCID 57664946HCID 57664946, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-{4-[(ethylamino)carbonyl]phenyl}-5-[(3-fluorophenoxy)methyl]-N-(2-hydroxyethyl)-1H-1,2,3-triazole-4-carboxamide (600 mg) obtained in Example 498 in THF (15 ml) were added ethyl chlorocarbonate (0.15 ml) and pyridine (0.17 ml), and the mixture was stirred under ice-cooling for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (ethyl acetate/hexane=3/1 to ethyl acetate) and recrystallized from ethyl acetate to give the title compound as a colorless powder (520 mg).

Workup

  1. temperaturecooling for 4 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column (ethyl acetate/hexane=3/1 to ethyl acetate)
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f399a561b33f48a9ad57b36e76b274eb
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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