تفاعل #72511

معادلة التفاعل

ethyl acetate

6-chloro-11H-benzo[e]pyrido[3,2-b][1,4]diazepine

diisopropylethylamine

tert-butyl 4-(hydrazinecarbonyl)phenethylcarbamate

→

tert-butyl 4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)phenethylcarbamate

المذيبات

N,N-dimethylacetamide

ظروف التفاعل

المعالجة

1. 1
   workup.WAIT100° C. for an additional 48 hours
2. 2
   غسيلwashed with water (2×700 mL)
3. 3
   تجفيفThe organic layer was dried over anhydrous magnesium sulfate
4. 4
   أخرىevaporated to dryness
5. 5
   أخرىto give a brown foam
6. 6
   أخرىThis residue was purified by silica gel chromatography
7. 7
   غسيلeluting with ethyl acetate in hexanes (75-80%)
8. 8
   أخرىto give a brown foam that
9. 9
   أخرىwas crystallized from dichloromethane

الإجراء التجريبي

To a solution of 6-chloro-11H-benzo[e]pyrido[3,2-b][1,4]diazepine (822 mg, 3.58 mmol) and diisopropylethylamine (2 mL) in N,N-dimethylacetamide (25 mL) was added tert-butyl 4-(hydrazinecarbonyl)phenethylcarbamate (1.0 g, 3.58 mmol). The mixture was stirred at 80° C. for 24 hours then 100° C. for an additional 48 hours. The mixture was poured into ethyl acetate (150 mL) and washed with water (2×700 mL). The organic layer was dried over anhydrous magnesium sulfate and evaporated to dryness to give a brown foam. This residue was purified by silica gel chromatography eluting with ethyl acetate in hexanes (75-80%) to give a brown foam that was crystallized from dichloromethane to yield tert-butyl 4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)phenethylcarbamate as off white crystals (717 mg). M.p.=145-148° C.; 400 MHz 1H NMR (CDCl3) δ: 8.21-8.17 (m, 2H), 7.44-7.37 (m, 3H), 7.24-7.16 (m, 3H), 7.0 (dd, J=1.6, 8.4 Hz, 2H), 6.82-6.79 (m, 1H), 6.38 (s, 1H), 4.55 (br.s, 1H), 3.42-3.37 (m, 2H), 2.84 (t, J=7.2 Hz, 2H), 1.44 (s, 9H). LCMS [M+H]: 455.

المصدر