Reaktion #218099

Reaktionsgleichung

ethyl acetate

6-(2,3,4,5-tetrahydro-1H-benzo[c]azepin-7-yloxy)nicotinamide

K2CO3

1-bromohexane

→

title compound

6-(2-Hexyl-2,3,4,5-tetrahydro-1H-benzo[c]azepin-7-yloxy)nicotinamide

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturincrease the temperature to 100° C. for additional two hours
2. 2
   TemperaturCool the reaction mixture to room temperature
3. 3
   WaschenWash with 1.0 N NaOH (1×50 mL), brine (1×50 mL)
4. 4
   Trocknendry the organic layer over Na2SO4
5. 5
   Filtrationfilter
6. 6
   Einengenconcentrate
7. 7
   SonstigePurify by flash chromatography
8. 8
   Wascheneluting with 7% to 15% (2.0 M NH3 in methanol) in ethyl acetate

Vorschrift

Mix 6-(2,3,4,5-tetrahydro-1H-benzo[c]azepin-7-yloxy)nicotinamide (Example 447, Part E, 0.300 g, 1.06 mmol), K2CO3 (0.366 g, 2.65 mmol), and 1-bromohexane (0.192 g, 1.16 mmol) in DMF (5.3 mL). Heat at 70° C. overnight, then increase the temperature to 100° C. for additional two hours. Cool the reaction mixture to room temperature and add ethyl acetate (150 mL). Wash with 1.0 N NaOH (1×50 mL), brine (1×50 mL), dry the organic layer over Na2SO4, filter and concentrate. Purify by flash chromatography eluting with 7% to 15% (2.0 M NH3 in methanol) in ethyl acetate to give the title compound: MS ES+368.2 (M+H)+, HRMS calcd for C22H30N3O2 368.2338 (M+H)+, found 368.2334, time 0.53 min; HPLC [YMC-Pro pack C-18 (150×4.6 mm, S-5 microm), 0.05% TFA/acetonitrile in 0.05% TFA/water at 1.0 mL/min, 10-20% over 5 min, 20-95% over 18 min], tR=11.6 min, 97.8% purity.

Quelle