تفاعل #218101

معادلة التفاعل

ethyl acetate

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

K2CO3

4-(3-chloropropyl)morpholine

→

title compound

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

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةCool the reaction mixture to room temperature
2. 2
   غسيلWash with 1.0 N NaOH (1×50 mL), brine (1×50 mL)
3. 3
   تجفيفdry the organic layer over Na2SO4
4. 4
   ترشيحfilter
5. 5
   تركيزconcentrate
6. 6
   أخرىPurify by flash chromatography
7. 7
   غسيلeluting with 10% (2.0 M NH3 in methanol) in acetone

الإجراء التجريبي

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 4-(3-chloropropyl)morpholine (0.191 g, 1.16 mmol) in DMF (5.3 mL). Heat at 90° C. overnight. 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 10% (2.0 M NH3 in methanol) in acetone to give the title compound: MS ES+411.2 (M+H)+, HRMS calcd for C23H31N4O3 411.2396 (M+H)+, found 411.2389, time 0.48 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=5.7 min, 100% purity.

المصدر