Water → 7-(Bicyclo[2.2.1]hept-1-yl)-6-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine

HRID 380319Notes

Reaction equation

HRID 380319 reaction equation
[C:1]12([C:8]3[C:13](Cl)=[N:12][N:11]4[C:15]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)=[N:16][N:17]=[C:10]4[CH:9]=3)[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[CH3:24][N:25]1[C:29]([CH2:30][OH:31])=[N:28][CH:27]=[N:26]1.[H-].[Na+].O>CN(C)C=O>[C:1]12([C:8]3[C:13]([O:31][CH2:30][C:29]4[N:25]([CH3:24])[N:26]=[CH:27][N:28]=4)=[N:12][N:11]4[C:15]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)=[N:16][N:17]=[C:10]4[CH:9]=3)[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 11073377(1-methyl-1H-1,2,4-triazol-5-yl)methanolHCID 538792557-(Bicyclo[2.2.1]hept-1-yl)-6-chloro-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine

Product 1

HCID 99090267-(Bicyclo[2.2.1]hept-1-yl)-6-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(bicyclo[2.2.1]hept-1-yl)-6-chloro-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine (0.125 g, 0.39 mM) and (2-methyl-2H-1,2,4-triazol-3-yl)methanol (0.08 g, 0.47 mM; prepared using the conditions described in EP-A-421210) in N,N-dimethylformamide (20 ml) was added sodium hydride (0.015 g of a 60% dispersion in oil, 0.47 mM eq) and the reaction mixture was stirred at room temperature for 3 hours. Water was added until the solution became cloudy and after stirring for a further 15 minutes a solid was collected by filtration. This solid was recrystallised from ethyl acetate-dichloromethane to give the required product (0.048 g, m.p.=244-246° C.). 1H NMR (360 MHz, DMSO) δ1.39 (2H, m), 1.67-1.84 (8H, m), 2.30 (1H, m), 3.93 (3H, s), 5.70 (2H, s), 7.52-7.62 (3H, m), 8.00 (1H, s), 8.35 (1H, s), 8.38 (2H, m); (Regiochemistry was established using nOe data). MS (ES+) m/e 402 [MH]+. Anal. Found C, 65.71; H, 5.65; N, 24.07. C22H23N7O requires C, 65.82; H, 5.77; N, 24.42%.

Workup

  1. customprepared
  2. stirringafter stirring for a further 15 minutes a solid
  3. filtrationwas collected by filtration
  4. customThis solid was recrystallised from ethyl acetate-dichloromethane

Sources & evidence

ORD record
ord-587c8feacb94489b9709ecd7c4198651
Source dataset
uspto-grants-2001_10
Patent number
US06303597B1

Reaction notes

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