Benzoylhydrazine → Toluene-4-sulfonic acid 3-cyclopentyl-4-methyl-7-phenylpyrazolo[1,5-d][1,2,4]triazin-2-yl ester

HRID 985426Notes

Reaction equation

HRID 985426 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[CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)(=O)[CH3:2].[C:25]([NH:33][NH2:34])(=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>C1(C)C(C)=CC=CC=1>[CH:20]1([C:5]2[C:6]([O:9][S:10]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)(=[O:12])=[O:11])=[N:7][N:8]3[C:4]=2[C:1]([CH3:2])=[N:34][N:33]=[C:25]3[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 11955BenzoylhydrazineHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 86587506toluene-4-sulfonic acid 5-acetyl-4-cyclopentyl-1H-pyrazol-3-yl ester

Product 1

HCID 86587509Toluene-4-sulfonic acid 3-cyclopentyl-4-methyl-7-phenylpyrazolo[1,5-d][1,2,4]triazin-2-yl ester

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
180 °C

Procedure

Toluene-4-sulfonic acid 5-acetyl-4-cyclopentyl-1H-pyrazol-3-yl ester (0.65 g, 1.87 mmol) and benzhydrazide (0.28 g, 1.1 molar eq) were stirred together in xylene (20 ml) at reflux for 2.5 h. The solvent was reduced to ˜5 ml and Dowtherm A (20 ml) was added and the reaction mixture was heated at 180° C. for 2 h. The mixture was cooled and poured directly onto a column of silica gel, and the Dowtherm was eluted off with dichloromethane before eluting the product off with 3-6% ethyl acetate in dichloromethane (UV detection). Toluene-4-sulfonic acid 3-cyclopentyl-4-methyl-7-phenylpyrazolo[1,5-d][1,2,4]triazin-2-yl ester was obtained as a light brown solid (0.62 g). 1H NMR (360 MHz, CDCl3) δ 1.73-2.07 (8H, m), 2.49 (3H, s), 2.91 (3H, s), 3.48 (1H, m), 7.26-7.61 (5H, m), 7.93-7.97 (2H, m), 8.13-8.15 (2H, d, J=8.7 Hz); MS (ES+) m/e 449 [MH]+.

Workup

  1. temperatureat reflux for 2.5 h
  2. additionwas added
  3. temperatureThe mixture was cooled
  4. additionpoured directly onto a column of silica gel
  5. washthe Dowtherm was eluted off with dichloromethane
  6. washbefore eluting the product off with 3-6% ethyl acetate in dichloromethane (UV detection)

Sources & evidence

ORD record
ord-7c1a0bd8ab234e53a67dc3168f2416cc
Source dataset
uspto-grants-2005_03
Patent number
US06872720B2

Reaction notes

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