Potassium Carbonate → 3-Cyclopentyl-2-(2-ethyl-2h-[1,2,4]triazol-3-ylmethoxy)-5-methyl-8-phenylimidazo[1,2-d][1,2,4]triazine

HRID 396157Notes

Reaction equation

HRID 396157 reaction equation
[CH:1]1([C:6]2[N:10]3[C:11]([CH3:21])=[N:12][N:13]=[C:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:9]3=[N:8][C:7]=2[OH:22])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.Cl[CH2:25][C:26]1[N:27]([CH2:31][CH3:32])[N:28]=[CH:29][N:30]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:1]1([C:6]2[N:10]3[C:11]([CH3:21])=[N:12][N:13]=[C:14]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:9]3=[N:8][C:7]=2[O:22][CH2:25][C:26]2[N:27]([CH2:31][CH3:32])[N:28]=[CH:29][N:30]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 230031843-Cyclopentyl-5-methyl-8-phenylimidazo[1,2-d][1,2,4]triazin-2-olHCID 230031925-(chloromethyl)-1-ethyl-1H-1,2,4-triazole hydrochloride

Product 1

HCID 99310163-Cyclopentyl-2-(2-ethyl-2h-[1,2,4]triazol-3-ylmethoxy)-5-methyl-8-phenylimidazo[1,2-d][1,2,4]triazineYield 18.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-cyclopentyl-5-methyl-8-phenylimidazo[1,2-d][1,2,4]triazin-2-ol (175 mg, 0.59 mmol) and 3-chloromethyl-2-ethyl-2H-[1,2,4]triazole hydrochloride (130 mg, 0.71 mmol) in anhydrous N,N-dimethylformamide under an atmosphere of nitrogen was added potassium carbonate (329 mg, 2.37 mmol). The reaction mixture was stirred at room temperature for 3 h, then evaporated in vacuo. The residue was purified by flash chromatography (SiO2; 2% MeOH in CH2Cl2), and the product recrystallised from ethyl acetate/isohexane to afford the title compound (45 mg) as a white solid, m.p. 94-96° C.; δH (400 MHz; CDCl3) 1.44 (3H, t, J 7.2), 1.65-2.04 (8H, m), 3.01 (3H, s), 3.70 (1H, m), 4.29 (2H, q, J 7.2), 5.65 (2H, s), 7.52-7.60 (3H, m), 7.91 (1H, s), 8.10 (2H, m); m/z (ES+) 404 (M++H, 100%).

Workup

  1. customevaporated in vacuo
  2. customThe residue was purified by flash chromatography (SiO2; 2% MeOH in CH2Cl2)
  3. customthe product recrystallised from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-8a76856fe61d4fdca825db49c5aa93dc
Source dataset
uspto-grants-2003_08
Patent number
US06608062B1

Reaction notes

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