Reaktion #1870972

Reaktionsgleichung

3-chloroaniline

triethylamine

3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine-1-carbonyl chloride hydrochloride

→

title compound

Ausbeute 35.2%

3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine-1-carboxylic acid (3-chloro-phenyl)-amide

Ausbeute 35.2%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthen washed with sat. aq. NaHCO3 (20 mL)
2. 2
   SonstigeThe organic layer was separated
3. 3
   Extraktionthe aqueous layer was extracted with dichloromethane (20 mL)
4. 4
   TrocknenThe combined organic layers were dried over anhydrous sodium sulfate
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residue was chromatographed on silica

Vorschrift

To a solution of 3-chloroaniline (0.060 mL, 0.54 mmol) and triethylamine (0.16 mL, 1.14 mmol) in CH2Cl2 (10 mL) was added 3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine-1-carbonyl chloride hydrochloride (150 mg, 0.45 mmol). The mixture was stirred at ambient temperature for 1 h then washed with sat. aq. NaHCO3 (20 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (20 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica to yield the title compound (61 mg, 35%). 1H NMR (DMSO-d6) δ 10.0 (1H), 8.45 (1H), 8.15 (2H), 7.81 (1H), 7.35 (1H), 7.20 (1H), 7.10 (1H), 6.94 (1H), 3.49 (4H), 3.26 (2H), 2.81 (2H), 2.44 (4H); m/z (M+H)=385.18.

Quelle