反応 #743093

反応方程式

3-(azidomethy)-2-phenylquinoline-4-carboxylic acid

3-(azidomethyl)-2-phenylquinoline-4-carboxylic acid

HOBT hydrate

4-methylmorpholine

EDC

(S)-1-Phenyl propylamine

→

title compound

収率 73.0%

3-(azidomethyl)-2-phenyl-N-[(1s)-1-phenylpropyl]quinoline-4-carboxamide

収率 73.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他All solvent was removed in vacuo
2. 2
   その他the residue was partitioned between ethyl acetate and 10% aqueous sodium bicarbonate solution
3. 3
   乾燥dried over sodium sulfate
4. 4
   濃縮concentrated in vacuo
5. 5
   その他The residue was purified by chromatography
6. 6
   洗浄eluting with 15-25% ethyl acetate/hexane

実験手順

A solution of 3-(azidomethy)-2-phenylquinoline-4-carboxylic acid (2c) (997 mg, 3.28 mmol), HOBT hydrate (760 mg, 4.92 mmol), 4-methylmorpholine (551 μL, 4.92 mmol) in tetrahydrofuran (50 mL) was added EDC (960 mg, 4.92 mmol) at RT under N2. (S)-1-Phenyl propylamine (488.5 mg, 3.62 mmol) was then added and the reaction mixture stirred at RT for 12 h. All solvent was removed in vacuo and the residue was partitioned between ethyl acetate and 10% aqueous sodium bicarbonate solution, dried over sodium sulfate and then concentrated in vacuo. The residue was purified by chromatography eluting with 15-25% ethyl acetate/hexane to give the title compound (1000 mg, 73%) as a light-yellow solid. 1H NMR (300 MHz, CDCl3) δ 0.94 (t, 3H), 2.01 (m, 2H), 5.17 (q, 1H), 5.19 (s, 2H), 5.72 (b, 1H), 7.21 (d, 2H), 7.34 (d, 2H), 7.39 (m, 1H), 7.78 (m, 2H), 7.84 (m, 2H), 8.08 (m, 1H), 8.30 (m, 2H), 8.49 (m, 2H). MS APCI, m/z=422 (M+1). LCMS: 2.47 min.

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