N-(thioacetyl)-2,4-dichlorobenzamide → 4-(2,4-Dichlorophenyl)-8-(3-pentyl)-7-ethyl-2-methyl-pyrazolo[1,5-a]-1,3,5-triazine

HRID 1061542Notes

Reaction equation

HRID 1061542 reaction equation
[C:1]([NH:4][C:5](=O)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13])(=S)[CH3:2].[NH2:15][C:16]1[C:20]([CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[C:19]([CH2:26][CH3:27])[NH:18][N:17]=1>O1CCOCC1>[Cl:13][C:7]1[CH:8]=[C:9]([Cl:12])[CH:10]=[CH:11][C:6]=1[C:5]1[N:17]2[N:18]=[C:19]([CH2:26][CH3:27])[C:20]([CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[C:16]2[N:15]=[C:1]([CH3:2])[N:4]=1

Participants

4

Reactant 2

HCID 22184681N-(thioacetyl)-2,4-dichlorobenzamideHCID 221846823-Amino-5-ethyl-4-(3-pentyl)pyrazole

Product 1

HCID 52513414-(2,4-Dichlorophenyl)-8-(3-pentyl)-7-ethyl-2-methyl-pyrazolo[1,5-a]-1,3,5-triazineYield 25.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-(thioacetyl)-2,4-dichlorobenzamide (200 mg, 0.81 mmol) and 3-amino-5-ethyl-4-(3-pentyl)pyrazole (146 mg, 0.81 mmol) in dioxan (1 mL) was stirred at reflux temperature for 16 h. After being cooled to room temperature, the reaction mixture was concentrated in vacuo. Preparative TLC using EtOAc:hexanes::1:1 generated the title product (77.3 mg, 24% yield): mp=91-93° C.; NMR (CDCl3,300 MHz): δ 7.64 (d, 1H, J=8), 7.57 (d, 1H, J=2), 7.44 (dd, 1H, J=8,2), 2.77 (q, 2H, J=8), 2.69 (s, 3H), 2.80-2.60 (m, 1H), 2.00-1.80 (m, 4H), 1.25 (t, 3H, J=8), 0.82 (t, 6H, J=7); CI-HRMS m/z Calcd: 377.1294, Found: 377.1303.

Workup

  1. temperatureat reflux temperature for 16 h
  2. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-d2a930ba73a44a6fb1ebec5123a82b21
Source dataset
uspto-grants-2005_11
Patent number
US06960583B2

Reaction notes

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