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

HRID 1263485
Notes
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Reaction equation

HRID 1263485 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 222853325-(chloromethyl)-1-methyl-1H-1,2,4-triazole hydrochlorideHCID 1354097283,4-dihydro-3-phenyl-5H-pyrazolo[3,4-c]isoquinolin-5-one

Product 1

HCID 98850395-(2-Methyl-2H-[1,2,4]triazol-3-ylmethoxy)-3-phenyl-3H-pyrazolo[3,4-c]isoquinolineYield 74%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

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

  1. filtrationthe mixture was filtered
  2. washThe solids were washed with diethyl ether (5 ml)
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes