تفاعل #1167398

معادلة التفاعل

8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester

3-(dimethylamino)pyrrolidine

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title product

8-(3-Dimethylaminopyrrolidinyl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic Acid Acetic Acid Salt

المذيبات

pyridine

pyridine

ظروف التفاعل

المعالجة

1. 1
   أخرىThe pyridine was removed under vacuum
2. 2
   استخلاصthe product was extracted with chloroform
3. 3
   تجفيفAfter drying over MgSO4
4. 4
   أخرىthe solvent was removed
5. 5
   أخرىthe residue was purified by chromatography on silica gel
6. 6
   غسيلeluting with 100:40:20:8 chloroform

الإجراء التجريبي

A 81 mg sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, was dissolved in 2.5 mL of dry pyridine under a nitrogen atmosphere. To this solution was added a solution of 114 g of 3-(dimethylamino)pyrrolidine in 2.5 mL of pyridine, and the reaction mixture was heated at 60° C. for 39 hours. The pyridine was removed under vacuum, and the residue was stirred with 1N NaOH in THF/water for at 60° C. for 6 hours. The solution was made acidic with acetic acid, and the product was extracted with chloroform. After drying over MgSO4, the solvent was removed, and the residue was purified by chromatography on silica gel, eluting with 100:40:20:8 chloroform: methanol: acetic acid:water to give the title product. mp 165-170° C. (dec.). MS 374 (M+H)+ ; 1H NMR (D6 -DMSO) δ: 0.53 (m, 2H), 0.82-1.08 (m, 2H), 1.75 (s, 3H), 2.22 (s, 6H), 2.08-2.33 (m, 2H), 2.74 (m, 2H), 3.44-3.94 (m, 5H), 8.01 (br, s, 1H), 8.90 (br s, 1H).

المصدر