{2-[5-[2-(dioxo-lambda~6~-sulfanyl)-4-pyrimidinyl]-4-(4-fluorophenyl)-1H-imidazol-2-yl]-5-methyl-1,3-dioxan-5-yl}(4-methyl-1-piperazinyl)methanone -Drug Synthesis Database

【结构式】

【分子编号】62745

【品名】{2-[5-[2-(dioxo-lambda~6~-sulfanyl)-4-pyrimidinyl]-4-(4-fluorophenyl)-1H-imidazol-2-yl]-5-methyl-1,3-dioxan-5-yl}(4-methyl-1-piperazinyl)methanone

【CA登记号】

【分子式】C₂₄H₂₇FN₆O₅S

【分子量】530.5802232

【元素组成】C 54.33% H 5.13% F 3.58% N 15.84% O 15.08% S 6.04%

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：(XVI)

Attachment of the sulfonylpyrimidine (X) to a Merrifield thiol resin in the presence of NaH in DMF provides resin-bounded compound (XI). Then, saponification of the methyl ester group of (XI) yields carboxylic acid (XII). After formation of the corresponding acid chloride (XIII), coupling with N-methylpiperazine (XIV) gives rise to amide (XV). Sulfide group oxidation in (XV) leads to the sulfonylpyrimidine resin (XVI). Finally, cleavage from the resin in the presence of cyclopropylmethylamine (XVII) in hot NMP affords the target 2-aminopyrimidine derivative

参考文献中间体

合成目标

【1】 McKenna, J.M.; Halley, F.; Souness, J.E.; McLay, I.M.; Pickett, S.D.; Collis, A.J.; Page, K.; Ahmed, I.; An algorithm-directed two-component library synthesized via solid-phase methodology yielding potent and orally bioavailable p38 MAP kinase inhibitors. J Med Chem 2002, 45, 11, 2173.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	62740	methyl 2-{4-(4-fluorophenyl)-5-[2-(methylsulfonyl)-4-pyrimidinyl]-1H-imidazol-2-yl}-5-methyl-1,3-dioxane-5-carboxylate		C₂₁H₂₁FN₄O₆S	详情	详情
(XI)	62741	methyl 2-[4-(4-fluorophenyl)-5-(2-sulfanyl-4-pyrimidinyl)-1H-imidazol-2-yl]-5-methyl-1,3-dioxane-5-carboxylate		C₂₀H₁₉FN₄O₄S	详情	详情
(XII)	62742	2-[4-(4-fluorophenyl)-5-(2-sulfanyl-4-pyrimidinyl)-1H-imidazol-2-yl]-5-methyl-1,3-dioxane-5-carboxylic acid		C₁₉H₁₇FN₄O₄S	详情	详情
(XIII)	62743	2-[4-(4-fluorophenyl)-5-(2-sulfanyl-4-pyrimidinyl)-1H-imidazol-2-yl]-5-methyl-1,3-dioxane-5-carbonyl chloride		C₁₉H₁₆ClFN₄O₃S	详情	详情
(XIV)	10061	1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine	109-01-3	C₅H₁₂N₂	详情	详情
(XV)	62744	{2-[4-(4-fluorophenyl)-5-(2-sulfanyl-4-pyrimidinyl)-1H-imidazol-2-yl]-5-methyl-1,3-dioxan-5-yl}(4-methyl-1-piperazinyl)methanone		C₂₄H₂₇FN₆O₃S	详情	详情
(XVI)	62745	{2-[5-[2-(dioxo-lambda~6~-sulfanyl)-4-pyrimidinyl]-4-(4-fluorophenyl)-1H-imidazol-2-yl]-5-methyl-1,3-dioxan-5-yl}(4-methyl-1-piperazinyl)methanone		C₂₄H₂₇FN₆O₅S	详情	详情
(XVII)	59524	Aminomethylcyclopropane; Cyclopropanemethylamine	2516-47-4	C₄H₉N	详情	详情

Extended Information