1-(2,4-dichloro-3-[[(2-methyl-8-quinolinyl)oxy]methyl]phenyl)-1H-pyrrole-2-carbonitrile -Drug Synthesis Database

【结构式】

【分子编号】19302

【品名】1-(2,4-dichloro-3-[[(2-methyl-8-quinolinyl)oxy]methyl]phenyl)-1H-pyrrole-2-carbonitrile

【CA登记号】

【分子式】C₂₂H₁₅Cl₂N₃O

【分子量】408.28612

【元素组成】C 64.72% H 3.7% Cl 17.37% N 10.29% O 3.92%

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：(IX)

Benzyl alcohol (I) was treated with mesyl chloride and triethylamine in CH2Cl2 at 0 C, and the resulting mesylate (II) was subsequently coupled with 2-methyl-8-hydroxyquinoline (III) in the presence of NaH to afford ether (IV). Reduction of the nitro group of (IV) with hydrazine in the presence of FeCl3 and carbon gave aniline (V). Pyrrole (VII) was then obtained by heating (V) with 2,5-dimethoxy tetrahydrofuran (VI) in AcOH. Further reaction of (VII) with chlorosulfonylisocyanate (VIII) at low temperature provided the 2-cyanopyrrole (IX). The cyano group of (IX) was reduced with LiAlH4 to give amine (X). This was finally condensed with pyridinylacrylic acid (XI) using EDC and HOBt to yield the target amide, which was isolated as the dihydrochloride salt.

参考文献中间体

合成目标

【1】 Abe, Y.; Kayakiri, H.; Satoh, S.; Inoue, T.; Sawada, Y.; Inamura, N.; Asano, M.; Aramori, I.; Hatori, C; Sawai, H.; Oku, T.; Tanaka, H.; A novel class of orally active non-peptide bradykinin B2 receptor antagonists. 4. Discovery of novel frameworks mimicking the active conformation. J Med Chem 1998, 41, 23, 4587.

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)	18590	(2,6-dichloro-3-nitrophenyl)methanol		C₇H₅Cl₂NO₃	详情	详情
(II)	19295	2,6-dichloro-3-nitrobenzyl methanesulfonate		C₈H₇Cl₂NO₅S	详情	详情
(III)	18598	2-methyl-8-quinolinol	826-81-3	C₁₀H₉NO	详情	详情
(IV)	18926	(E)-3-[4-[(methylamino)carbonyl]phenyl]-2-propenoic acid		C₁₁H₁₁NO₃	详情	详情
(V)	18930	2,4-dichloro-3-[[(2-methyl-8-quinolinyl)oxy]methyl]phenylamine; 2,4-dichloro-3-[[(2-methyl-8-quinolinyl)oxy]methyl]aniline		C₁₇H₁₄Cl₂N₂O	详情	详情
(VI)	12132	2,5-Dimethoxytetrahydrofuran; 5-Methoxytetrahydro-2-furanyl methyl ether	696-59-3	C₆H₁₂O₃	详情	详情
(VII)	19300	2,6-dichloro-3-(1H-pyrrol-1-yl)benzyl 2-methyl-8-quinolinyl ether; 8-[[2,6-dichloro-3-(1H-pyrrol-1-yl)benzyl]oxy]-2-methylquinoline		C₂₁H₁₆Cl₂N₂O	详情	详情
(VIII)	14010	ethyl 5-(2-chlorophenyl)-2-hydrazino-3,6,7,9-tetrahydro-8H-pyrido[4',3':4,5]thieno[2,3-e][1,4]diazepine-8-carboxylate		C₁₉H₂₀ClN₅O₂S	详情	详情
(IX)	19302	1-(2,4-dichloro-3-[[(2-methyl-8-quinolinyl)oxy]methyl]phenyl)-1H-pyrrole-2-carbonitrile		C₂₂H₁₅Cl₂N₃O	详情	详情
(X)	19303	[1-(2,4-dichloro-3-[[(2-methyl-8-quinolinyl)oxy]methyl]phenyl)-1H-pyrrol-2-yl]methanamine; [1-(2,4-dichloro-3-[[(2-methyl-8-quinolinyl)oxy]methyl]phenyl)-1H-pyrrol-2-yl]methylamine		C₂₂H₁₉Cl₂N₃O	详情	详情
(XI)	19304	(E)-3-[6-(acetamido)-3-pyridinyl]-2-propenoic acid		C₁₀H₁₀N₂O₃	详情	详情

Extended Information