4-(Acetamido)-5-chloro-2-methoxybenzoyl chloride -Drug Synthesis Database

【结构式】

【分子编号】11631

【品名】4-(Acetamido)-5-chloro-2-methoxybenzoyl chloride

【CA登记号】

【分子式】C₁₀H₉Cl₂NO₃

【分子量】262.0918

【元素组成】C 45.83% H 3.46% Cl 27.05% N 5.34% O 18.31%

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：(IV)

The reaction of quinolizidinone (I) with hydroxylamine and pyridine in refluxing ethanol gives the corresponding oxime (II), which is reduced with LiAlH4 in ether to yield 6-methyl-2-aminoquinolizidine (III). The acylation of (III) with 4-acetamido-5-chloro-2-methoxybenzoyl chloride (IV) [prepared from the corresponding acid (V) and SOCl2] by means of triethylamine in benzene affords the protected benzamide (VI), which is finally deprotected with KOH in refluxing ethanol.

参考文献中间体

合成目标

【1】 Hadley, M.S.; Watts, E.A. (SmithKline Beecham plc); Treating gastro-intestinal disorders and emesis with n-(heterocyclic substituted)benzamides. BE 0860049; DE 2748260; FR 2370051; GB 1593146; JP 53059692; NL 7712203; US 4213983 .
【2】 Singh, S.K.; Kumar, Y.; Prasad, M.; Prasad, A.; Kumar, N.P. (Ranbaxy Laboratories Ltd.); Process for the preparation of cefdinir. WO 0391261 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	29171	6-methyloctahydro-2H-quinolizin-2-one	C₁₀H₁₇NO	详情	详情
(II)	29172	6-methyloctahydro-2H-quinolizin-2-one oxime	C₁₀H₁₈N₂O	详情	详情
(III)	29173	6-methyloctahydro-2H-quinolizin-2-amine	C₁₀H₂₀N₂	详情	详情
(IV)	11631	4-(Acetamido)-5-chloro-2-methoxybenzoyl chloride	C₁₀H₉Cl₂NO₃	详情	详情
(V)	29174	4-(acetamido)-5-chloro-2-methoxybenzoic acid	C₁₀H₁₀ClNO₄	详情	详情
(VI)	29175	4-(acetamido)-5-chloro-2-methoxy-N-(6-methyloctahydro-2H-quinolizin-2-yl)benzamide	C₂₀H₂₈ClN₃O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

A new synthesis of renzapride has been described: The reaction of 1-azabicyclo[3.3.1]nonan-4-one (I) with hydroxylamine and pyridine in refluxing ethanol gives the corresponding oxime (II), which is reduced with Na in refluxing pentanol yielding a mixture of the exo- and endo-amines (IIIa and IIIb). The acylation of this mixture with 4-acetamido-5-chloro-2-methoxybenzoylchloride (IV) and triethylamine in toluene affords a mixture of the exo- and endo-amides (Va and Vb), which are separated by column chromatography over alumina. The endo-isomer (Va) is finally deacetylated with NaOH in refluxing ethanol. It is obtained as crystals, m.p. > 260 C.

参考文献中间体

合成目标

【1】 Hadley, M.S.; Smith, D.M.; Watts, E.A.; Joiner, K.T.; Martin, R.T.; Sanger, G.J.; Smith, G.E.; King, F.D.; Smith, P.; Turner, D.H.; Substituted benzamides with conformationally restricted side chains.5. Azabicyclo[x.y.z]derivatives as 5-HT4 receptor agonists and gastric motility stimulants. J Med Chem 1993, 36, 6, 683.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(IIIa)	11629	(R)-1-Azabicyclo[3.3.1]non-4-ylamine; (R)-1-Azabicyclo[3.3.1]nonan-4-amine	C₈H₁₆N₂	详情	详情
(IIIb)	11630	(S)-1-Azabicyclo[3.3.1]nonan-4-amine; (S)-1-Azabicyclo[3.3.1]non-4-ylamine	C₈H₁₆N₂	详情	详情
(Va)	11632	4-(Acetamido)-N-(1-azabicyclo[3.3.1]non-4-yl)-5-chloro-2-methoxybenzamide	C₁₈H₂₄ClN₃O₃	详情	详情
(Vb)	11633	4-(Acetamido)-N-(1-azabicyclo[3.3.1]non-4-yl)-5-chloro-2-methoxybenzamide	C₁₈H₂₄ClN₃O₃	详情	详情
(I)	11627	1-Azabicyclo[3.3.1]nonan-4-one	C₈H₁₃NO	详情	详情
(II)	11628	1-Azabicyclo[3.3.1]nonan-4-one oxime	C₈H₁₄N₂O	详情	详情
(IV)	11631	4-(Acetamido)-5-chloro-2-methoxybenzoyl chloride	C₁₀H₉Cl₂NO₃	详情	详情

Extended Information