Benzoylhydrazine → HCID 86587505, compound

HRID 985421Notes

Reaction equation

HRID 985421 reaction equation
[C:1]([C:4]1[NH:8][N:7]=[C:6]([O:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[C:5]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[F:26])(=O)[CH3:2].[C:27]([NH:35][NH2:36])(=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C(C)=CC=CC=1>[F:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:5]1[C:6]([O:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[N:7][N:8]2[C:4]=1[C:1]([CH3:2])=[N:36][N:35]=[C:27]2[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 11955BenzoylhydrazineHCID 86587503HCID 86587503, compound

Product 1

HCID 86587505HCID 86587505, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Toluene-4-sulfonic acid 5acetyl-4-(2-fluorophenyl)-1H-pyrazol-3-yl ester (1.0 g, 2.7 mmol; prepared as described in Example 1, steps a to c) was stirred with benzhydrazide (400 mg, 2.9 mmol) in xylene (30 ml) at reflux overnight. The mixture was allowed to cool to room temperature. A solid crystallised out of solution This was separated by filtration, and was recrystallised from ethyl acetate, yielding toluene-4-sulfonic acid 3-(2-fluorophenyl)-4-methyl-7-phenylpyrazolo[1,5-d][1,2,4]triazin-2-yl ester as a white solid (694 mg). 1H NMR (400 MHz, CDCl3) δ 2.47 (3H, s), 2.52 (3H, s), 7.19 (1H, t, J=8.9 Hz), 7.28 (3H, m), 7.41-7.52 (4H, m), 7.61 (1H, m), 7.79 (2H, d, J=8.3 Hz), 8.25 (2H, d, J=7.5 Hz); MS (ES+) m/e 475 [MH]+.

Workup

  1. customprepared
  2. temperatureat reflux overnight
  3. customA solid crystallised out of solution
  4. customThis was separated by filtration
  5. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-95c1bdba5e1e469a967d81a2526f8c44
Source dataset
uspto-grants-2005_03
Patent number
US06872720B2

Reaction notes

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