반응 #73653

반응 방정식

2-benzoylamino-4-methylthiazole-5-carbonyl chloride

cyclopropylmethylamine

pyridine

→

title compound

수율 45.0%

2-Benzoylamino-4-methylthiazole-5-carboxylic Acid Cyclopropylmethylamide

수율 45.0%

용매

dichloromethane

tetrahydrofuran

dichloromethane

반응 조건

후처리

1. 1
   세척washed with 1 N hydrochloric acid (5 mL), saturated aqueous sodium bisulfate (2×5 mL), and brine (5 mL)
2. 2
   건조dried over anhydrous sodium sulfate
3. 3
   여과filtered
4. 4
   농축The filtrate was concentrate in vacuo
5. 5
   기타the residue was purified by column chromatography

실험 절차

To a cooled mixture of cyclopropylmethylamine (0.033 g, 0.46 mmol), pyridine (0.090 g, 1.14 mmol) and 4-dimethylaminoyridine (0.010 mg) in anhydrous tetrahydrofuran was added 2-benzoylamino-4-methylthiazole-5-carbonyl chloride (0.079 g, 0.038 mmol) in anhydrous dichloromethane (1 mL) dropwise. The reaction mixture was stirred at ambient temperature for 2 h, then diluted with dichloromethane (10 mL), washed with 1 N hydrochloric acid (5 mL), saturated aqueous sodium bisulfate (2×5 mL), and brine (5 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrate in vacuo and the residue was purified by column chromatography to afford the title compound as a white solid in 45% yield (45 mg); m.p. 163-166° C.; 1H NMR (CDCl3, 300 MHz) δ 7.89 (d, J=7.9 Hz, 2H), 7.57 (t, J=7.4 Hz, 1H), 7.45 (t, J=7.5 Hz, 2H), 5.84 (s, 1H), 3.23 (dd, J=5.4, 7.1 Hz, 2H), 2.23 (s, 3H), 1.00-0.98 (m, 1H), 0.53 (q, J=5.8 Hz, 2H), 0.22 (q, J=5.0 Hz, 2H); MS (ES+) m/z 316.1 (M+1).

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