반응 #647813

반응 방정식

2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

N,N-diisopropylethylamine

1-hydroxybenzotriazole

4-fluorobenzylamine

→

title compound

수율 58.0%

2-(3-benzyl-2-oxoimidazolidin-1-yl)-N-(4-fluorobenzyl)-4-methylthiazole-5-carboxamide

수율 58.0%

용매

ethyl acetate

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was kept stirring for 27 hours at ambient temperature
2. 2
   세척washed with water and brine
3. 3
   건조The organic solution was dried over anhydrous sodium sulfate
4. 4
   여과filtered
5. 5
   농축The filtrate was concentrated in vacuo
6. 6
   기타the residue was purified by column chromatography

실험 절차

To a solution of 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid (0.32 g, 1.00 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.20 g, 1.30 mmol) and N,N-diisopropylethylamine (0.50 mL, 2.80 mmol) in N,N-dimethylformamide (20 mL) was added 1-hydroxybenzotriazole (0.16 g, 1.20 mmol). The resulting mixture was stirred at ambient temperature for 15 minutes and 4-fluorobenzylamine (0.17 mL, 1.45 mmol) was added. The reaction mixture was kept stirring for 27 hours at ambient temperature, then was diluted with ethyl acetate (300 mL) and washed with water and brine. The organic solution was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo, and the residue was purified by column chromatography to afford the title compound as a white powder in 58% yield (0.25 g): mp 147-148° C.: 1H NMR (300 MHz. DMSO-6) δ 7.35-7.20 (m, 7H), 7.02-6.96 (m, 2H), 6.00 (s, 1H), 4.55-4.44 (m, 4H), 4.04 (t, J=7.5 Hz, 2H), 3.42 (t, J=7.5 Hz, 2H), 2.59 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 163.8, 162.4, 160.5, 157.3, 155.3, 153.2, 135.5, 133.8, 129.4, 128.9, 128.2, 117.0, 115.7, 47.9, 43.2, 42.0, 41.6, 17.1; MS (ES+) m/z 425.2 (M+1).

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