8-(acetamido)-7-chloro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】41271

【品名】8-(acetamido)-7-chloro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid

【CA登记号】

【分子式】C₁₁H₁₀ClNO₅

【分子量】271.65684

【元素组成】C 48.64% H 3.71% Cl 13.05% N 5.16% O 29.45%

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)

The chlorination of 8-acetamido-2,3-dihydro-1,4-benzodioxin-5-carboxylic acid (I) with chlorine in acetic acid gives the 7-chloro derivative (II), which is treated with aqueous NaOH to yield 8-amino-2,3-dihydro-1,4-benzodioxin-5-carboxylic acid (III). The reaction of (III) with carbonyldiimidazole (CDI) affords the activated intermediate (IV), which is finally condensed with 1-(1-butylpiperidin-4-yl)methanol (V) by means of MeLi in THF. The intermediate 1-(1-butylpiperidin-4-yl)methanol (V) has been obtained by condensation of piperidine-4-carboxylic acid ethyl ester (VI) with 1-bromobutane (VII) by means of K2CO3 in methanol, followed by reduction of the ester group with LiAlH4 in THF.

参考文献中间体

合成目标

【1】 Bulteau, G.; Acher, J.; Thominet, M.; Collignon, C. (Ile de France); Substituted 2,3-alkylenedioxybenzamides. DE 2734270; FR 2360305; GB 1571278; GB 1571447; JP 53018570; US 4186135; US 4248885; US 4255580 .
【2】 Gaster, L.M.; Sanger, G.J.; SB-204070: 5-HT4 receptor antagonists and their potential therapeutic utility. Drugs Fut 1994, 19, 12, 1109.

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)	41270	8-(acetamido)-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid		C₁₁H₁₁NO₅	详情	详情
(II)	41271	8-(acetamido)-7-chloro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid		C₁₁H₁₀ClNO₅	详情	详情
(III)	41272	8-amino-7-chloro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid		C₉H₈ClNO₄	详情	详情
(IV)	41273	(8-amino-7-chloro-2,3-dihydro-1,4-benzodioxin-5-yl)(1H-imidazol-1-yl)methanone		C₁₂H₁₀ClN₃O₃	详情	详情
(V)	41274	(1-butyl-4-piperidinyl)methanol		C₁₀H₂₁NO	详情	详情
(VI)	17410	Ethyl isonipecotate; ethyl 4-piperidinecarboxylate	1126-09-6	C₈H₁₅NO₂	详情	详情
(VII)	28721	1-bromobutane	109-65-9	C₄H₉Br	详情	详情

Extended Information