Reaktion #1909248

Reaktionsgleichung

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

Ausbeute 73.0%

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

Ausbeute 73.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAll solvent was removed in vacuo
2. 2
   Sonstigethe residue was partitioned between ethyl acetate and 10% aqueous sodium bicarbonate solution
3. 3
   Trocknendried over sodium sulfate
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe residue was purified by chromatography
6. 6
   Wascheneluting with 15-25% ethyl acetate/hexane

Vorschrift

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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