2-Fluorobenzhydrazide → HCID 86587504, compound

HRID 985419Notes

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].[F:27][C:28]1[CH:37]=[CH:36][CH:35]=[CH:34][C:29]=1[C:30]([NH:32][NH2:33])=O>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:33][N:32]=[C:30]2[C:29]1[CH:34]=[CH:35][CH:36]=[CH:37][C:28]=1[F:27]

Participants

Conditions

Temperature: 180 °C

Procedure

Toluene-4-sulfonic acid 5-acetyl-4-(2-fluorophenyl)-1H-pyrazol-3-yl ester (8.26 g, 22.1 mmol) and 2-fluorobenzhydrazide (3.86 g, 25.0 mmol) were stirred together in xylene (250 ml) at reflux overnight. The solvent was removed in vacuo, and the residue was heated in Dowtherm A at 180° C. for 2 h. The mixture was poured directly onto a column of silica gel, and the Dowtherm was eluted off with dichloromethane before eluting the product off with 10% ethyl acetate in dichloromethane (UV detection). Toluene-4-sulfonic acid 3,7-bis(2-fluorophenyl)-4-methylpyrazolo[1,5-d][1,2,4]triazin-2-yl ester was obtained as a yellow solid (6.62 g). 1H NMR (400 MHz, CDCl3) δ 2.43 (3H, s), 2.53 (3H, s), 7.17-7.37 (6H, m), 7.41-7.51 (2H, m), 7.63 (1H, m), 7.69 (3H, m); MS (ES+) m/e 493 [MH]+.

Workup

temperatureat reflux overnight
customThe solvent was removed in vacuo
additionThe mixture was poured directly onto a column of silica gel
washthe Dowtherm was eluted off with dichloromethane
washbefore eluting the product off with 10% ethyl acetate in dichloromethane (UV detection)

Sources & evidence

ORD record: ord-09be482b1831440e952659b800f1e5c8
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872720B2

Reaction notes

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