Hydrazine hydrate (1:1) → 2-[3-(4-Chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetohydrazide

HRID 714617Notes

Reaction equation

HRID 714617 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH2:17][C:18](O)=[O:19])[N:9]=2)=[CH:4][CH:3]=1.C[Si](C=[N+:26]=[N-:27])(C)C.O.NN>CO.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH:13]3[CH2:14][CH2:15]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:26][NH2:27])=[O:19])[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 167693TrimethylsilyldiazomethaneHCID 42632357[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acid

Product 1

HCID 674061412-[3-(4-Chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetohydrazide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

50 mg (0.17 mmol) of [3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acid [preparation according to WO 2007/134862 Example 88A] were dissolved in 0.4 ml of methanol and diluted with 0.6 ml of toluene, and 128 μl (0.26 mmol) of trimethylsilyldiazomethane solution (2 M in hexanes) were then added dropwise until a slight yellow color remained. The reaction was stirred for 1 h and then evaporated to dryness. The residue was taken up in 1 ml of ethanol, 43 mg (0.85 mmol) of hydrazine hydrate were added and the mixture was stirred under reflux for 2.5 h. After cooling, the solution was concentrated under reduced pressure and the residue was dried under high vacuum. This gave 54 mg (96% of theory) of the title compound in a purity of 93% as a colorless solid.

Workup

  1. additionwere then added dropwise until a slight yellow color
  2. customevaporated to dryness
  3. stirringthe mixture was stirred
  4. temperatureunder reflux for 2.5 h
  5. temperatureAfter cooling
  6. concentrationthe solution was concentrated under reduced pressure
  7. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-ebe5eb9a487b4938b2eed207000806e5
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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