N-[3-[(3-isocyanato-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)methyl]phenyl]-N'-isopropylurea -Drug Synthesis Database

【结构式】

【分子编号】26158

【品名】N-[3-[(3-isocyanato-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)methyl]phenyl]-N'-isopropylurea

【CA登记号】

【分子式】C₂₂H₂₄N₄O₃

【分子量】392.45772

【元素组成】C 67.33% H 6.16% N 14.28% O 12.23%

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)

Treatment of 3-aminobenzyl alcohol (I) with isopropyl isocyanate produced urea (II). Mesylation of alcohol (III), followed by reaction with LiBr gave benzyl bromide (III). Then, alkylation of 3-azidobenzazepine (IV) with (III) under phase-transfer conditions afforded (V). The azido group of (V) was reduced to amine (VI) by catalytic hydrogenation over Pd/C. Subsequent treatment of (VI) with carbonyl diimidazole produced isocyanate (VII). This was finally converted to the target compound by condensation with 6-aminobenzothiazole (VIII).

参考文献中间体

合成目标

【1】 Hara, H.; Murakami, Y.; Okada, T.; et al.; 1,3-Disubstituted benzazepines as novel, potent, selective neuropeptide Y Y1 receptor antagonists. J Med Chem 1999, 42, 14, 2621.

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)	26153	(3-aminophenyl)methanol	1877-77-6	C₇H₉NO	详情	详情
(II)	26154	N-[3-(hydroxymethyl)phenyl]-N'-isopropylurea		C₁₁H₁₆N₂O₂	详情	详情
(III)	26155	N-[3-(bromomethyl)phenyl]-N'-isopropylurea		C₁₁H₁₅BrN₂O	详情	详情
(IV)	20891	3-azido-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one		C₁₀H₁₀N₄O	详情	详情
(V)	26156	N-[3-[(3-azido-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)methyl]phenyl]-N'-isopropylurea		C₂₁H₂₄N₆O₂	详情	详情
(VI)	26157	N-[3-[(3-amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)methyl]phenyl]-N'-isopropylurea		C₂₁H₂₆N₄O₂	详情	详情
(VII)	26158	N-[3-[(3-isocyanato-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)methyl]phenyl]-N'-isopropylurea		C₂₂H₂₄N₄O₃	详情	详情
(VIII)	17908	1,3-benzothiazol-6-ylamine; 1,3-benzothiazol-6-amine; 6-Aminobenzothiazole	533-30-2	C₇H₆N₂S	详情	详情

Extended Information