Triethylamine → HCID 57422493, compound

HRID 1686363Notes

Reaction equation

HRID 1686363 reaction equation
[CH2:1]([N:8]([C:10]([NH:12][C:13]1[CH:14]=[N:15][N:16]([CH2:18][C:19]2[C:20]([CH3:25])=[N:21][O:22][C:23]=2[CH3:24])[CH:17]=1)=[O:11])[NH2:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:27](OCC)=[O:28].C(N(CC)CC)C.[OH-].[Na+]>C(#N)C>[CH2:1]([N:8]1[C:10](=[O:11])[N:12]([C:13]2[CH:14]=[N:15][N:16]([CH2:18][C:19]3[C:20]([CH3:25])=[N:21][O:22][C:23]=3[CH3:24])[CH:17]=2)[C:27](=[O:28])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 57422496HCID 57422496, compound

Product 1

HCID 57422493HCID 57422493, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

1-benzyl-N-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)hydrazinecarboxamide (2.00 g, 5.88 mmol), ethyl chlorformate (6.38 g, 58.77 mmol), and triethylamine (1.78 g, 17.63 mmol) in acetonitrile (50 mL) were heated at 100° C. for 48 hours. The mixture was cooled to 80° C., 1 M NaOH (aq) (5 mL) was added and the reaction mixture was stirred for 1 hour. The reaction was cooled to room temperature and concentrated on the rotpvap. The residue was dissolved in dichloromethane and filtered to remove salts and the solution was concentrated to afford 1-benzyl-4-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1,2,4-triazolidine-3,5-dione (1.28 g, 60%) as a yellow oil. MS M+H calculated 367.14. found 367.2.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated on the rotpvap
  3. dissolutionThe residue was dissolved in dichloromethane
  4. filtrationfiltered
  5. customto remove salts
  6. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-580b3a1190544f3ea3e225aa9b555fca
Source dataset
uspto-grants-2012_04
Patent number
US08148544B2

Reaction notes

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