6-ethyl-8-iodo-2,3-dihydro-4(1H)-quinolinone -Drug Synthesis Database

【结构式】

【分子编号】60626

【品名】6-ethyl-8-iodo-2,3-dihydro-4(1H)-quinolinone

【CA登记号】

【分子式】C₁₁H₁₂INO

【分子量】301.12689

【元素组成】C 43.88% H 4.02% I 42.14% N 4.65% O 5.31%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

Condensation of 4-ethylaniline (I) with propiolactone (II) produces the beta-aminoacid (III). Intramolecular Friedel-Crafts cyclization of (III) by means of polyphosphoric acid leads to the quinolinone (IV). Then, electrophilic iodination of (IV) by using iodine monochloride provides the intermediate (V)

参考文献中间体

合成目标

【1】 Jarvest, R.L.; Berge, J.M.; Berry, V.; et al.; Nanomolar inhibitors of Staphylococcus aureus methionyl tRNA synthetase with potent antibacterial activity against Gram-positive pathogens. J Med Chem 2002, 45, 10, 1959.
【2】 Berge, J.M.; Forrest, A.K.; Elder, J.S.; Jarvest, R.L. (GlaxoSmithKline plc); Quinolones as t-RNA synthetase inhibitors and antibacterial agents. WO 0021949 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	60623	4-ethylaniline; 4-ethylphenylamine		C₈H₁₁N	详情	详情
(II)	24477	2-oxetanone	57-57-8	C₃H₄O₂	详情	详情
(III)	60624	3-(4-ethylanilino)propanoic acid		C₁₁H₁₅NO₂	详情	详情
(IV)	60625	6-ethyl-2,3-dihydro-4(1H)-quinolinone		C₁₁H₁₃NO	详情	详情
(V)	60626	6-ethyl-8-iodo-2,3-dihydro-4(1H)-quinolinone		C₁₁H₁₂INO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

Displacement of 2-chloro-4-ethoxyquinoline (VI) with 1,3-propanediamine (VII) affords the aminoquinoline (VIII). Subsequent acidic hydrolysis of (VIII) provides quinolinone (IX). Finally, reductive condensation between amine (IX) and ketone (V) in the presence of NaBH3CN leads to the target disubstituted propanediamine

参考文献中间体

合成目标

【1】 Jarvest, R.L.; Berge, J.M.; Berry, V.; et al.; Nanomolar inhibitors of Staphylococcus aureus methionyl tRNA synthetase with potent antibacterial activity against Gram-positive pathogens. J Med Chem 2002, 45, 10, 1959.
【2】 Berge, J.M.; Forrest, A.K.; Elder, J.S.; Jarvest, R.L. (GlaxoSmithKline plc); Quinolones as t-RNA synthetase inhibitors and antibacterial agents. WO 0021949 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	60626	6-ethyl-8-iodo-2,3-dihydro-4(1H)-quinolinone		C₁₁H₁₂INO	详情	详情
(VI)	60627	2-chloro-4-ethoxyquinoline; 2-chloro-4-quinolinyl ethyl ether		C₁₁H₁₀ClNO	详情	详情
(VII)	19331	3-aminopropylamine; 1,3-propanediamine	109-76-2	C₃H₁₀N₂	详情	详情
(VIII)	60628	N-(3-aminopropyl)-N-(4-ethoxy-2-quinolinyl)amine; N~1~-(4-ethoxy-2-quinolinyl)-1,3-propanediamine		C₁₄H₁₉N₃O	详情	详情
(IX)	60629	2-[(3-aminopropyl)amino]-4(1H)-quinolinone		C₁₂H₁₅N₃O	详情	详情

Extended Information