Water → HCID 68517260, compound

HRID 1717351Notes

Reaction equation

HRID 1717351 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([C:13]([NH:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:9][C:8]=1[N:18]1[CH:22]=[C:21]([C:23]([NH:25][CH:26]2[CH2:28][CH2:27]2)=[O:24])[N:20]=[N:19]1.O>CN(C=O)C>[CH:26]1([NH:25][C:23]([C:21]2[N:20]=[N:19][N:18]([C:8]3[CH:9]=[CH:10][C:11]([C:13]([NH:15][CH2:16][CH3:17])=[O:14])=[CH:12][C:7]=3[O:6][CH:5]=[CH2:4])[CH:22]=2)=[O:24])[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 57665096HCID 57665096, compound

Product 1

HCID 68517260HCID 68517260, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (0.06 g, purity 60%) in DMF (5 ml) was added 1-{2-(2-chloroethoxy)-4-[(ethylamino)carbonyl]phenyl}-N-cyclopropyl-1H-1,2,3-triazole-4-carboxamide (0.19 g) obtained in Example 150, and the mixture was stirred at 0° C. for 30 min and at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. 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=1/1 to ethyl acetate) and recrystallized from ethanol-water to give the title compound as a pale-yellow powder (0.02 g, 13%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate)
  5. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-6b66c9b7184f4807be01e73326ae5dfb
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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