2-Fluorobenzhydrazide → Toluene-4-sulfonic acid 7-(2-fluorophenyl)-4-methylpyrazolo[1,5-d][1,2,4]triazin-2-yl ester

HRID 985439Notes

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])[CH:5]=1)(=O)[CH3:2].[F:20][C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[C:23]([NH:25][NH2:26])=O>C1(C)C(C)=CC=CC=1>[F:20][C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[C:23]1[N:8]2[N:7]=[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])[CH:5]=[C:4]2[C:1]([CH3:2])=[N:26][N:25]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of toluene-4-sulfonic acid 5-acetyl-1H-pyrazol-3-yl ester (2.52 g, 8.99 mmol) and 2-fluorobenzhydrazide (1.53 g, 9.90 mmol) in xylene (110 ml) was heated at reflux for 17 h under nitrogen. The solvent was removed in vacuo, and the residue was heated in Dowtherm A at 180° C. for 18 h The mixture was poured directly onto a column of silica gel, which was eluted with dichloromethane, then 25% EtOAc/CH2Cl2, to give 3.40 g (95%) of the title compound as a brown solid: 1H NMR (360 MHz, CDCl3) δ 2.45 (3H, s), 2.83 (3H, s), 6.71 (1H, s), 7.18 (1H, t, J=9.5 Hz), 7.30 (2H, d, J=7.8 Hz), 7.31 (1H, m), 7.59 (1H, m), 7.66 (1H, m), 7.82 (2H, d, J=8.4 Hz); MS (ES+) m/e 399 [M+H]+.

Workup

temperaturewas heated
temperatureat reflux for 17 h under nitrogen
customThe solvent was removed in vacuo
additionwas poured directly onto a column of silica gel, which
washwas eluted with dichloromethane

Sources & evidence

ORD record: ord-8728c22d9aab44889d516e5e6531c6cd
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872720B2

Reaction notes

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