HRID973462

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6996

2-Chlorobenzaldehyde

C7H5ClO

HCID4193550

未命名化合物

结构：CCOC(=O)CC(=O)c1ccc(-n2c(C)nc3cnccc32)nc1

HCID54245582

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)C1=C(c2ccc(-n3c(C)nc4cnccc43)nc2)NC(C)=C(C(=O)Nc2ccccn2)C1c1ccccc1Cl

HCID15045523

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID702

Ethanol

C2H6O

PROCEDURE

实验过程

A solution of ethyl 2-(2-methylimidazo[4,5-c]pyrid-1-yl)pyrid-5-oylacetate (324 mg, 1.0 mmol), 3-amino-N-(2-pyridyl)-but-2-enamide (178 mg, 1.0 mmol) and 2-chlorobenzaldehyde (140 mg, 1.0 mmol) in ethanol (4 ml) was heated under reflux for 5 hours under nitrogen. The solution was cooled and concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with ethyl acetate:methanol, 6:1), followed by sonication of a suspension of the eluted product in ether/ethyl acetate, 3:1 for 45 minutes. The off-white solid product was filtered off and dried in vacuo to give the title compound, 140 mg (23%), m.p. 242°-3° C.

WORKUP

后处理

temperatureunder reflux for 5 hours under nitrogen
temperatureThe solution was cooled
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography (eluting with ethyl acetate:methanol, 6:1)
customfollowed by sonication of a suspension of the eluted product in ether/ethyl acetate
filtrationThe off-white solid product was filtered off
customdried in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ca672c9209ce44c08c89f928551b5dab
来源数据集: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05063237
来源说明: uspto-grants-1991_11

反应 SMILES

[CH3:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=O)=[CH:13][N:12]=2)[C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1.[NH2:25][C:26]([CH3:37])=[CH:27][C:28]([NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)=[O:29].[Cl:38][C:39]1[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=1[CH:41]=O>C(O)C>[Cl:38][C:39]1[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=1[CH:41]1[C:27]([C:28](=[O:29])[NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)=[C:26]([CH3:37])[NH:25][C:17]([C:14]2[CH:15]=[CH:16][C:11]([N:3]3[C:4]4[CH:9]=[CH:8][N:7]=[CH:6][C:5]=4[N:10]=[C:2]3[CH3:1])=[N:12][CH:13]=2)=[C:19]1[C:20]([O:22][CH2:23][CH3:24])=[O:21]