N-methyl(4-nitrophenyl)methanamine -Drug Synthesis Database

【结构式】

【分子编号】28426

【品名】N-methyl(4-nitrophenyl)methanamine

【CA登记号】

【分子式】C₈H₁₀N₂O₂

【分子量】166.17968

【元素组成】C 57.82% H 6.07% N 16.86% O 19.26%

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)

Silylated 4-oxoazetidine-2-carboxylic acid (I) was converted to the mixed anhydride with isobutyl chloroformate, and then reduced to alcohol (II) with NaBH4. Subsequent Mitsunobu coupling of (II) with mercaptotetrazole (III) provided thioether (IV). Desilylation of (IV) was then achieved by treatment with CsF in MeOH to give (V). Reaction of 4-nitrobenzyl chloride (VI) with methylamine afforded secondary amine (VII). This was reacted with phosgene and diisopropyl ethylamine to produce the carbamoyl chloride (VIII). Finally, condensation of this chloride with azetidinone (V) in the presence of lithium bis(trimethylsilyl)amide furnished the target urea.

参考文献中间体

合成目标

【1】 Yoakim, C.; Ogilvie, W.W.; Cameron, D.R.; Chabot, C.; Grand-Maitre, C.; Guse, I.; Hache, B.; Kawai, S.; Naud, J.; O'Meara, J.A.; Plante, R.; Deziel, R.; Potent beta-lactam inhibitors of human cytomegalovirus protease. Antivir Chem Chemother 1998, 9, 5, 379.

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)	28418	(2R)-1-[tert-butyl(dimethyl)silyl]-4-oxo-2-azetidinecarboxylic acid		C₁₀H₁₉NO₃Si	详情	详情
(II)	28419	(4R)-1-[tert-butyl(dimethyl)silyl]-4-(hydroxymethyl)-2-azetidinone		C₁₀H₂₁NO₂Si	详情	详情
(III)	28420	5-Mercapto-1-methyl-1H-tetrazole; 1-Methyl-1H-1,2,3,4-tetraazol-5-ylhydrosulfide	13183-79-4	C₂H₄N₄S	详情	详情
(IV)	28421	(4R)-1-[tert-butyl(dimethyl)silyl]-4-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-2-azetidinone		C₁₂H₂₃N₅OSSi	详情	详情
(V)	28422	(4R)-4-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-2-azetidinone		C₆H₉N₅OS	详情	详情
(VI)	22580	1-(chloromethyl)-4-nitrobenzene	100-14-1	C₇H₆ClNO₂	详情	详情
(VII)	28426	N-methyl(4-nitrophenyl)methanamine		C₈H₁₀N₂O₂	详情	详情
(VIII)	28427	1-[[(chlorocarbonyl)(methyl)amino]methyl]-4-nitrobenzene		C₉H₉ClN₂O₃	详情	详情

Extended Information