5-bromo-N-(4-fluorobenzyl)-8-hydroxy[1,6]naphthyridine-7-carboxamide -Drug Synthesis Database

【结构式】

【分子编号】57748

【品名】5-bromo-N-(4-fluorobenzyl)-8-hydroxy[1,6]naphthyridine-7-carboxamide

【CA登记号】

【分子式】C₁₆H₁₁BrFN₃O₂

【分子量】376.1847632

【元素组成】C 51.09% H 2.95% Br 21.24% F 5.05% N 11.17% O 8.51%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(VII)

Mitsunobu coupling between isopropyl 3-(hydroxymethyl)pyridine-2-carboxylate (I) and N-tosyl glycine methyl ester (II) affords amino diester (III). Diester (III) is subsequently converted to the naphthyridine (IV) under Dieckmann cyclization conditions. Bromination of naphthyridine (IV) by means of N-bromosuccinimide provides (V). The methyl ester group of (V) is then displaced with 4-fluorobenzylamine (VI) to furnish amide (VII). Finally, copper-catalyzed displacement of the bromide (VII) with butanesultam (VIII) provides the title compound.

参考文献中间体

合成目标

【1】 Young, S.D.; Guare, J.P.; Wai, J.S.; Fisher, T.E.; Perlow, D.S.; Anthony, N.J.; Egbertson, M.; Gomez, R.P.; Kuo, M.S.; Tran, L.; Zhuang, L.; Langford, H.M.; Melamed, J.Y.; Bennett, J.J.; Embrey, M.; Jolly, S.M.; Funk, T.W. (Merck & Co., Inc.); Aza- and polyaza-naphthalenyl carboxamides useful as HIV integrase inhibitors. WO 0230930; WO 0230931 .

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)	57743	isopropyl 3-(hydroxymethyl)-2-pyridinecarboxylate		C₁₀H₁₃NO₃	详情	详情
(II)	57744	methyl 2-{[(4-methylphenyl)sulfonyl]amino}acetate	2645-02-5	C₁₀H₁₃NO₄S	详情	详情
(III)	57745	isopropyl 3-({(2-methoxy-2-oxoethyl)[(4-methylphenyl)sulfonyl]amino}methyl)-2-pyridinecarboxylate		C₂₀H₂₄N₂O₆S	详情	详情
(IV)	57746	methyl 8-hydroxy[1,6]naphthyridine-7-carboxylate		C₁₀H₈N₂O₃	详情	详情
(V)	57747	methyl 5-bromo-8-hydroxy[1,6]naphthyridine-7-carboxylate		C₁₀H₇BrN₂O₃	详情	详情
(VI)	31095	4-fluorobenzylamine; (4-fluorophenyl)methanamine	140-75-0	C₇H₈FN	详情	详情
(VII)	57748	5-bromo-N-(4-fluorobenzyl)-8-hydroxy[1,6]naphthyridine-7-carboxamide		C₁₆H₁₁BrFN₃O₂	详情	详情
(VIII)	57749	1lambda~6~,2-thiazinane-1,1-dione		C₄H₉NO₂S	详情	详情

Extended Information