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