Water → 5-(2-Methyl-2H-[1,2,4]triazol-3-ylmethoxy)-3-phenyl-3H-pyrazolo[3,4-c]isoquinoline

HRID 1263485Notes

Reaction equation

[C:1]1([N:7]2[C:11]3[NH:12][C:13](=[O:20])[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:10]=3[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl[CH2:23][C:24]1[N:25]([CH3:29])[N:26]=[CH:27][N:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH3:29][N:25]1[C:24]([CH2:23][O:20][C:13]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:10]3[CH:9]=[N:8][N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:11]=3[N:12]=2)=[N:28][CH:27]=[N:26]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 3,4-dihydro-3-phenyl-5H-pyrazolo[3,4-c]isoquinolin-5-one (0.10 g, 0.38 mmol), 3-chloromethyl-2-methyl-2H-[1,2,4]triazole hydrochloride (0.10 g, 0.57 mmol) and cesium carbonate (0.37 g, 1.14 mmol) in dry DMF (2 ml) was stirred at 60° C. under nitrogen for 3 h. Water (30 ml) was added and the mixture was filtered. The solids were washed with diethyl ether (5 ml) and dried in vacuo to give the title compound (0.10 g, 74%) as an off-white powder, m.p. 149-151° C. Found: C, 66.19; H, 4.46; N, 23.71. C20H16N6O.0.25(H2O) requires C, 66.56; H, 4.61; N, 23.29%. δH (400 MHz; CDCl3) 3.98 (3H, s), 5.82 (2H, s), 7.36 (1H, dd, J=7 and 7), 7.52-7.57 (3H, m), 7.83 (1H, dd, J=7 and 7), 7.94 (1H, s), 8.15-8.20 (3H, m), 8.33 (1H, d, J=8), 8.42 (1H, s); m/z (ES+) 356 (M+H+).

Workup

filtrationthe mixture was filtered
washThe solids were washed with diethyl ether (5 ml)
customdried in vacuo

Sources & evidence

ORD record: ord-873d0beeef8144cf8fc203ae967bf58b
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06541484B2

Reaction notes

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