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【结 构 式】

【分子编号】29201

【品名】N-[4-(3-cyano-2-methylpropanoyl)phenyl]acetamide

【CA登记号】

【 分 子 式 】C13H14N2O2

【 分 子 量 】230.26644

【元素组成】C 67.81% H 6.13% N 12.17% O 13.9%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(V)

Friedel-Crafts acylation of acetanilide (I) with propionyl chloride in the presence of AlCl3 afforded 4'-(acetamido)propiophenone (II). Subsequent Mannich reaction of (II) with dimethylamine hydrochloride and formaldehyde produced the aminoketone (III). Quaternization of the tertiary amine of (III) with MeI, followed by displacement of the resulting ammonium salt (IV) with KCN yielded the intermediate ketonitrile (V). In alternative procedure, nitrile (V) was prepared by acylation of acetanilide (I) with 3-chloro-2-methylpropionyl chloride, and further displacement of the resulting beta-chloroketone (VI) with KCN. Acid hydrolysis of both nitrile and acetamido groups of (V) provided ketoacid (VII), which was cyclized with hydrazine to give pyridazinone (VIII). Finally, acylation of the amino group of (VIII) by means of pyridine-2-carbonyl chloride furnished the title amide.

1 Liu, C.M.; et al.; Synthesis and platelet aggregation inhibitory activity of 6-(4'-substituted acylaminophenyl)-4,5-dihydro-3-(2H)-pyridazinones. Acta Pharm Sin 1999, 34, 1, 23.
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) 10194 N-Phenylacetamide; Acetanilide 103-84-4 C8H9NO 详情 详情
(II) 29198 N-(4-propionylphenyl)acetamide C11H13NO2 详情 详情
(III) 29199 N-[4-[3-(dimethylamino)-2-methylpropanoyl]phenyl]acetamide C14H20N2O2 详情 详情
(IV) 29200 3-[4-(acetamido)phenyl]-N,N,N,2-tetramethyl-3-oxo-1-propanaminium iodide C15H23IN2O2 详情 详情
(V) 29201 N-[4-(3-cyano-2-methylpropanoyl)phenyl]acetamide C13H14N2O2 详情 详情
(VI) 29202 N-[4-(3-chloro-2-methylpropanoyl)phenyl]acetamide C12H14ClNO2 详情 详情
(VII) 29203 4-(4-aminophenyl)-3-methyl-4-oxobutyric acid C11H13NO3 详情 详情
(VIII) 29204 6-(4-aminophenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone C11H13N3O 详情 详情
(IX) 29205 2-pyridinecarbonyl chloride C6H4ClNO 详情 详情

合成路线2

该中间体在本合成路线中的序号:(V)

Friedel-Crafts acylation of acetanilide (I) with propionyl chloride in the presence of AlCl3 afforded 4'-(acetamido)propiophenone (II). Subsequent Mannich reaction of (II) with dimethylamine hydrochloride and formaldehyde produced the aminoketone (III). Quaternization of the tertiary amine of (III) with MeI, followed by displacement of the resulting ammonium salt (IV) with KCN yielded the intermediate ketonitrile (V). In alternative procedure, nitrile (V) was prepared by acylation of acetanilide (I) with 3-chloro-2-methylpropionyl chloride, and further displacement of the resulting alpha-chloroketone (VI) with KCN. Acid hydrolysis of both nitrile and acetamido groups of (V) provided ketoacid (VII), which was cyclized with hydrazine to give pyridazinone (VIII). Finally, acylation of the amino group of (VIII) by means of pyridine-4-carbonyl chloride furnished the title amide.

1 Liu, C.M.; et al.; Synthesis and platelet aggregation inhibitory activity of 6-(4'-substituted acylaminophenyl)-4,5-dihydro-3-(2H)-pyridazinones. Acta Pharm Sin 1999, 34, 1, 23.
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) 10194 N-Phenylacetamide; Acetanilide 103-84-4 C8H9NO 详情 详情
(II) 29198 N-(4-propionylphenyl)acetamide C11H13NO2 详情 详情
(III) 29199 N-[4-[3-(dimethylamino)-2-methylpropanoyl]phenyl]acetamide C14H20N2O2 详情 详情
(IV) 29200 3-[4-(acetamido)phenyl]-N,N,N,2-tetramethyl-3-oxo-1-propanaminium iodide C15H23IN2O2 详情 详情
(V) 29201 N-[4-(3-cyano-2-methylpropanoyl)phenyl]acetamide C13H14N2O2 详情 详情
(VI) 29202 N-[4-(3-chloro-2-methylpropanoyl)phenyl]acetamide C12H14ClNO2 详情 详情
(VII) 29203 4-(4-aminophenyl)-3-methyl-4-oxobutyric acid C11H13NO3 详情 详情
(VIII) 29204 6-(4-aminophenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone C11H13N3O 详情 详情
(IX) 27850 isonicotinoyl chloride 39178-35-3 C6H4ClNO 详情 详情
Extended Information