2,4-dichloro-6-methyl-3-nitropyridine -Drug Synthesis Database

【结构式】

【分子编号】26787

【品名】2,4-dichloro-6-methyl-3-nitropyridine

【CA登记号】

【分子式】C₆H₄Cl₂N₂O₂

【分子量】207.01544

【元素组成】C 34.81% H 1.95% Cl 34.25% N 13.53% O 15.46%

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：(II)

4-Hydroxy-6-methyl-3-nitro-2-pyridone (I) was treated with phosphoryl chloride in boiling N,N-diethylaniline, and the resulting dichloropyridine (II) was condensed with n-butyl ethylamine (III) to afford a regioisomeric mixture of 4- (IV) and 2-amino (V) pyridines. After chromatographic separation, the desired isomer (IV) was coupled with 2-bromo-4-isopropylaniline (VI) at 140 C to provide (VII). Reduction of the nitro group of (VII) using sodium hydrosulfite and ammonia yielded diamine (VIII). Subsequent cyclization of (VIII) with phosgene in refluxing toluene gave imidazopyridinone (IX), which was finally N-methylated by means of CH3I and KOH in acetone.

参考文献中间体

合成目标

【1】 Beck, J.P.; et al.; Purin-8-ones as corticotropin-releasing hormone (CRH-R1) receptor antagonists. Bioorg Med Chem Lett 1999, 9, 7, 967.

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)	23337	4-hydroxy-6-methyl-3-nitro-2(1H)-pyridinone	4966-90-9	C₆H₆N₂O₄	详情	详情
(II)	26787	2,4-dichloro-6-methyl-3-nitropyridine		C₆H₄Cl₂N₂O₂	详情	详情
(III)	26788	N-butyl-N-ethylamine	13360-63-9	C₆H₁₅N	详情	详情
(IV)	26789	N-butyl-2-chloro-N-ethyl-6-methyl-3-nitro-4-pyridinamine		C₁₂H₁₈ClN₃O₂	详情	详情
(V)	26790	N-butyl-4-chloro-N-ethyl-6-methyl-3-nitro-2-pyridinamine		C₁₂H₁₈ClN₃O₂	详情	详情
(VI)	23782	2-bromo-4-isopropylaniline; 2-bromo-4-isopropylphenylamine	51605-97-1	C₉H₁₂BrN	详情	详情
(VII)	26791	N-[2-(2-bromo-4-isopropylanilino)-6-methyl-3-nitro-4-pyridinyl]-N-butyl-N-ethylamine		C₂₁H₂₉BrN₄O₂	详情	详情
(VIII)	26792	N-[3-amino-2-(2-bromo-4-isopropylanilino)-6-methyl-4-pyridinyl]-N-butyl-N-ethylamine		C₂₁H₃₁BrN₄	详情	详情
(IX)	26793	3-(2-bromo-4-isopropylphenyl)-7-[butyl(ethyl)amino]-5-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one		C₂₂H₂₉BrN₄O	详情	详情

Extended Information