N-(2,2-dimethyl-7-nitro-2H-chromen-6-yl)-2-(4-methoxyphenyl)acetamide -Drug Synthesis Database

【结构式】

【分子编号】26759

【品名】N-(2,2-dimethyl-7-nitro-2H-chromen-6-yl)-2-(4-methoxyphenyl)acetamide

【CA登记号】

【分子式】C₂₀H₂₀N₂O₅

【分子量】368.38928

【元素组成】C 65.21% H 5.47% N 7.6% O 21.72%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(III)

The condensation of 2,2-dimethyl-7-nitro-2H-1-benzopyran-6-amine (I) with 4-methoxyphenylacetyl chloride (II) by means of triethylmaine in chloroform gives the corresponding amide (III), which is regioselectively epoxidized with ClONa and a chiral manganese catalyst yielding the epoxide (IV). Finally, this compound is treated with cyclopropylamine in refluxing ethanol.

参考文献中间体

合成目标

【1】 Ohrai, K.; Sato, M.; Yanagihara, K.; Tanikawa, K.; Yamashita, T.; Shigeta, Y.; Structure-activity relationships and pharmacological activities of benzopyran derivatives with selective bradycardic and anti-fibrillatory effects. Symp Med Chem 1998, Abst 1-P-29.
【2】 Tanikawa, K.; Ohrai, K.; Sato, M.; Yamashita, T.; Yanagihara, K. (Nissan Chemical Industry, Ltd.); Chroman derivs.. EP 0934296; JP 1998087650; US 6066631; WO 9804542 .

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)	26757	2,2-dimethyl-7-nitro-2H-chromen-6-amine		C₁₁H₁₂N₂O₃	详情	详情
(II)	26758	2-(4-methoxyphenyl)acetyl chloride	4693-91-8	C₉H₉ClO₂	详情	详情
(III)	26759	N-(2,2-dimethyl-7-nitro-2H-chromen-6-yl)-2-(4-methoxyphenyl)acetamide		C₂₀H₂₀N₂O₅	详情	详情
(IV)	26760	N-[(1aR,7bR)-2,2-dimethyl-5-nitro-1a,7b-dihydro-2H-oxireno[2,3-c]chromen-6-yl]-2-(4-methoxyphenyl)acetamide		C₂₀H₂₀N₂O₆	详情	详情
(V)	12263	Cyclopropylamine; Cyclopropanamine	765-30-0	C₃H₇N	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The acylation of 6-amino-2,2-dimethyl-7-nitro-2H-1-benzopyran (I) with p-methoxyphenylacetyl chloride (II) furnished amide (III). Subsequent bromination of the pyran ring of (III) employing N-bromosuccinimide in H2O-DMSO formed the trans bromohydrin (IV), which was further cyclized to epoxide (V) upon treatment with NaOH. Finally, oxirane ring opening in (IV) with cyclopropylamine (VI) in boiling EtOH yielded the title trans amino alcohol.

参考文献中间体

合成目标

【1】 Tanikawa, K.; Ohrai, K.; Sato, M.; Yamashita, T.; Yanagihara, K. (Nissan Chemical Industry, Ltd.); Chroman derivs.. EP 0934296; JP 1998087650; US 6066631; WO 9804542 .

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)	26757	2,2-dimethyl-7-nitro-2H-chromen-6-amine		C₁₁H₁₂N₂O₃	详情	详情
(II)	26758	2-(4-methoxyphenyl)acetyl chloride	4693-91-8	C₉H₉ClO₂	详情	详情
(III)	26759	N-(2,2-dimethyl-7-nitro-2H-chromen-6-yl)-2-(4-methoxyphenyl)acetamide		C₂₀H₂₀N₂O₅	详情	详情
(IV)	59601	N-[(3S,4R)-3-bromo-4-hydroxy-2,2-dimethyl-7-nitro-3,4-dihydro-2H-chromen-6-yl]-2-(4-methoxyphenyl)acetamide		C₂₀H₂₁BrN₂O₆	详情	详情
(V)	26760	N-[(1aR,7bR)-2,2-dimethyl-5-nitro-1a,7b-dihydro-2H-oxireno[2,3-c]chromen-6-yl]-2-(4-methoxyphenyl)acetamide		C₂₀H₂₀N₂O₆	详情	详情
(VI)	12263	Cyclopropylamine; Cyclopropanamine	765-30-0	C₃H₇N	详情	详情

Extended Information