반응 #315556

반응 방정식

ethyl acetate

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

K2CO3

1-bromoheptane

→

title compound

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

용매

DMF

반응 조건

후처리

1. 1
   온도increase the temperature to 80° C. for 3.5 hours
2. 2
   온도Cool the reaction mixture to room temperature
3. 3
   세척Wash with water (1×30 mL), brine (1×30 mL)
4. 4
   건조dry the organic layer over NaSO4
5. 5
   여과filter
6. 6
   농축concentrate
7. 7
   기타Purify by flash chromatography
8. 8
   세척eluting with 6% to 15% (2.0 M NH3 in methanol) in ethyl acetate

실험 절차

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-bromoheptane (0.199 g, 1.11 mmol) in DMF (5.3 mL). Heat at 50° C. overnight, then increase the temperature to 80° C. for 3.5 hours. Cool the reaction mixture to room temperature and add ethyl acetate (100 mL). Wash with water (1×30 mL), brine (1×30 mL), dry the organic layer over NaSO4, filter and concentrate. Purify by flash chromatography eluting with 6% to 15% (2.0 M NH3 in methanol) in ethyl acetate to give the title compound: MS ES+ 382.2 (M+H)+, HRMS calcd for C23H32N3O2 382.2495 (M+H)+, found 382.2489, time 0.46 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=12.6 min, 98.6% purity.

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