1-(2,4-dichlorophenyl)-3-(dimethylamino)-2-(4-methyl-1H-imidazol-2-yl)-2-propen-1-one -Drug Synthesis Database

【结构式】

【分子编号】60242

【品名】1-(2,4-dichlorophenyl)-3-(dimethylamino)-2-(4-methyl-1H-imidazol-2-yl)-2-propen-1-one

【CA登记号】

【分子式】C₁₅H₁₅Cl₂N₃O

【分子量】324.20912

【元素组成】C 55.57% H 4.66% Cl 21.87% N 12.96% O 4.93%

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)

Acylation of 2,4-dimethylimidazole (I) with 2,4-dichlorobenzoyl chloride (II) in the presence of diisopropylethylamine, followed by acidic hydrolysis, provides the 2-imidazolyl acetophenone (III). Subsequent condensation of (III) with dimethylformamide dimethylacetal gives rise to the enaminone (IV)

参考文献中间体

合成目标

【1】 Brown, S.P.; Goff, D.; Ring, D.B.; Harrison, S.D.; Subramanian, S.; Nuss, J.M.; Boyce, R.S.; Johnson, K.; Pfister, K.B.; Ramurthy, S.; Renhowe, P.A.; Seely, L.; Wagman, A.S.; Zhou, X.A. (Chiron Corp.); Inhibitors of glycogen synthase kinase 3. EP 1087963; US 6417185; WO 9965897 .
【2】 Ring, D.B.; Harrison, S.D.; Nuss, J.M.; Boyce, R.S.; Johnson, K.; Pfister, K.B.; Ramurthy, S.; Seely, L.; Wagman, A.S.; Desai, M.; Levine, B.H. (Chiron Corp.); Inhibitors of glycogen synthase kinase 3. WO 0220495 .

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)	20613	2,4-dimethyl-1H-imidazole	930-62-1	C₅H₈N₂	详情	详情
(II)	35131	2,4-dichlorobenzoyl chloride; 2,4-Dichlorophenacylchloride	89-75-8	C₇H₃Cl₃O	详情	详情
(III)	60241	1-(2,4-dichlorophenyl)-2-(4-methyl-1H-imidazol-2-yl)-1-ethanone		C₁₂H₁₀Cl₂N₂O	详情	详情
(IV)	60242	1-(2,4-dichlorophenyl)-3-(dimethylamino)-2-(4-methyl-1H-imidazol-2-yl)-2-propen-1-one		C₁₅H₁₅Cl₂N₃O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

Condensation of 2-chloro-5-cyanopyridine (V) with ethylenediamine (VI) yields the N-pyridyl ethylenediamine (VII). Subsequent reaction of amine (VII) with pyrazole-1-carboxyamidine (VIII) in refluxing acetonitrile affords guanidine (IX). Finally, condensation between guanidine (IX) and enaminone (IV) in the presence of NaOEt produces the title pyrimidine derivative

参考文献中间体

合成目标

【1】 Brown, S.P.; Goff, D.; Ring, D.B.; Harrison, S.D.; Subramanian, S.; Nuss, J.M.; Boyce, R.S.; Johnson, K.; Pfister, K.B.; Ramurthy, S.; Renhowe, P.A.; Seely, L.; Wagman, A.S.; Zhou, X.A. (Chiron Corp.); Inhibitors of glycogen synthase kinase 3. EP 1087963; US 6417185; WO 9965897 .
【2】 Ring, D.B.; Harrison, S.D.; Nuss, J.M.; Boyce, R.S.; Johnson, K.; Pfister, K.B.; Ramurthy, S.; Seely, L.; Wagman, A.S.; Desai, M.; Levine, B.H. (Chiron Corp.); Inhibitors of glycogen synthase kinase 3. WO 0220495 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	60242	1-(2,4-dichlorophenyl)-3-(dimethylamino)-2-(4-methyl-1H-imidazol-2-yl)-2-propen-1-one		C₁₅H₁₅Cl₂N₃O	详情	详情
(V)	57164	2-Chloro-5-cyanopyridine; 6-Chloro-3-cyanopyridine; 6-Chloronicotinonitrile	33252-28-7	C₆H₃ClN₂	详情	详情
(VI)	14754	ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine；1,2-Ethanediamine	107-15-3	C₂H₈N₂	详情	详情
(VII)	54332	6-[(2-aminoethyl)amino]nicotinonitrile	n/a	C₈H₁₀N₄	详情	详情
(VIII)	15983	1H-pyrazole-1-carboximidamide	4023-00-1	C₄H₆N₄	详情	详情
(IX)	60243	N-{2-[(5-cyano-2-pyridinyl)amino]ethyl}guanidine		C₉H₁₂N₆	详情	详情

Extended Information