Reaktion #2368260

Reaktionsgleichung

potassium carbonate

iodomethane

3-{4-[4-Chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]benzyl}imidazolidine-2,4-dione

iodomethane

potassium carbonate

→

titled compound

3-{4-[4-Chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]benzyl}-1-methylimidazolidine-2,4-dione

Lösungsmittel

ethyl acetate

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITthe mixture was placed into a preheated oil bath at 50° C. for 2.5 hours
2. 2
   TemperaturThe mixture was cooled to ambient temperature
3. 3
   Waschenwashed with sodium bicarbonate (2×20 mL, aqueous saturated)
4. 4
   ExtraktionThe organic extract
5. 5
   Trocknenwas dried with sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe residue was purified by preparative reverse phase HPLC (85:15 to 36:64; water with 0.05% trifluoroacetic acid:acetonitrile with 0.05% trifluoroacetic acid)

Vorschrift

3-{4-[4-Chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]benzyl}imidazolidine-2,4-dione (Example 84, 19 mg, 0.048 mmol) was dissolved in N,N-dimethylformamide and treated with potassium carbonate (8.6 mg, 0.062 mmol, 1.3 equiv) and iodomethane (5.4 μL, 0.086 mmol, 1.8 equiv). After stirring at ambient temperature for 1 hour, additional iodomethane (5.4 μL, 0.086 mmol, 1.8 equiv) and potassium carbonate (8.6 mg, 0.062 mmol, 1.3 equiv) were added and the mixture was placed into a preheated oil bath at 50° C. for 2.5 hours. The mixture was cooled to ambient temperature, diluted with ethyl acetate (30 mL) and washed with sodium bicarbonate (2×20 mL, aqueous saturated). The organic extract was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by preparative reverse phase HPLC (85:15 to 36:64; water with 0.05% trifluoroacetic acid:acetonitrile with 0.05% trifluoroacetic acid) to afford the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 7.53 (1H, d, J=6.5 Hz); 7.51 (2H, d, J=6.7 Hz); 7.48 (2H, d, J=2.7 Hz); 7.45 (1H, d, J=2.9 Hz); 4.73 (2H, s); 4.55 (2H, d, J=7.2 Hz); 3.92 (2H, s); 3.02 (3H, s); 1.47-1.39 (1H, m); 0.72-0.67 (2H, m); 0.54-0.50 (2H, m) ppm; high resolution mass spectrometry (ES+) m/z 410.1380 [(M+H)+; calculated for C21H21ClN5O2: 410.1378].

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