5-(chloromethyl)-1-ethyl-1H-1,2,4-triazole hydrochloride → 5-(2-Ethyl-2H-[1,2,4]triazol-3-ylmethoxy)-3-phenyl-3H-pyrazolo[3,4-c]isoquinoline

HRID 1263486Notes

Reaction equation

HRID 1263486 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]([CH2:9][CH3:10])[N:6]=[CH:7][N:8]=1.[C:11]1([N:17]2[C:21]3[NH:22][C:23](=[O:30])[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=4[C:20]=3[CH:19]=[N:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:9]([N:5]1[C:4]([CH2:3][O:30][C:23]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=3[C:20]3[CH:19]=[N:18][N:17]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[C:21]=3[N:22]=2)=[N:8][CH:7]=[N:6]1)[CH3:10]

Participants

3

Reactant 2

HCID 230031925-(chloromethyl)-1-ethyl-1H-1,2,4-triazole hydrochlorideHCID 1354097283,4-dihydro-3-phenyl-5H-pyrazolo[3,4-c]isoquinolin-5-one

Product 1

HCID 101771765-(2-Ethyl-2H-[1,2,4]triazol-3-ylmethoxy)-3-phenyl-3H-pyrazolo[3,4-c]isoquinolineYield 76.5%

Procedure

Prepared as for Example 1, step c), using 3-chloromethyl-2 -ethyl-2H-[1,2,4]triazole hydrochloride (0.10 g, 0.55 mmol) and 3,4-dihydro-3-phenyl-5H-pyrazolo[3,4-c]isoquinolin-5-one (0.095 g, 0.36 mmol) to give the title compound (0.102 g, 76%) as an off-white powder, m.p. 147-148° C. Found: C, 66.49; H, 4.83; N, 22.16. C21H18N6O.0.5(H2O) requires C, 66.48; H, 5.05; N, 22.15%. δH (400 MHz; CDCl3) 1.47 (3H, t, J=7), 4.30 (2H, q, J=7), 5.82 (2H, s), 7.36 (1H, dd, J=8 and 7), 7.51-7.58 (3H, m), 7.83 (1H, dd, J=8 and 7), 7.96 (1H, s), 8.16 (1H, d, J=8), 8.22 (2H, d, J=8), 8.30 (1H, d, J=8), 8.42 (1H, s); m/z (ES+) 371 (M+H+).

Workup

  1. customPrepared as for Example 1, step c),

Sources & evidence

ORD record
ord-adb8f77b785f4211b1911ffcf15d1234
Source dataset
uspto-grants-2003_04
Patent number
US06541484B2

Reaction notes

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