HRID539805

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID14798

Sodium Hydroxide

HNaO

结构：CCOC(=O)C=Cc1cccc(C(=O)Nc2ccc3nc(-c4ccc(C)c(NC(=O)C(C)(C)C)c4)cn3n2)c1

HCID67983260

未命名化合物

PRODUCTS

生成物

结构：Cc1ccc(-c2cn3nc(NC(=O)c4cccc(C=CC(=O)O)c4)ccc3n2)cc1NC(=O)C(C)(C)C

HCID68089173

未命名化合物

收率 62.8%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID21899815

未命名化合物

CONDITIONS

反应条件

温度: 50 °C

PROCEDURE

实验过程

A 20-mL vial is charged with ethyl-3-[3-[[2-[3-(2,2-dimethylpropanoylamino)-4-methyl-phenyl]imidazo[2,1-f]pyridazin-6-yl]carbamoyl]phenyl]prop-2-enoate (0.042 g, 0.08 mmol) and a solution of THF-MeOH (1 mL, 1:1). To this mixture is added aqueous NaOH (1 mL, 1 M), then stirred at 50° C. for 1 hour. The mixture is concentrated to remove the organics and extracted with EtOAc once. Aqueous HCl (1M) is added to lower the pH to 2 and the resulting solids are filtered to give the title compound (0.025 g), which is used without further purification. LCMS (m/z)=498.5 [M+H]+, tR=2.47 min.

WORKUP

后处理

concentrationThe mixture is concentrated
customto remove the organics and
extractionextracted with EtOAc once
additionAqueous HCl (1M) is added
filtrationthe resulting solids are filtered

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-d010a2e2766649c184dce2e6e7f1dfb5
来源数据集: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08871767B2
来源说明: uspto-grants-2014_10

反应 SMILES

C([O:3][C:4](=[O:39])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13](=[O:38])[NH:14][C:15]2[CH:20]=[CH:19][C:18]3=[N:21][C:22]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([NH:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])[CH:25]=4)=[CH:23][N:17]3[N:16]=2)[CH:8]=1)C.[OH-].[Na+]>C1COCC1.CO>[CH3:34][C:33]([CH3:36])([CH3:35])[C:32]([NH:31][C:26]1[CH:25]=[C:24]([C:22]2[N:21]=[C:18]3[N:17]([CH:23]=2)[N:16]=[C:15]([NH:14][C:13]([C:9]2[CH:8]=[C:7]([CH:6]=[CH:5][C:4]([OH:39])=[O:3])[CH:12]=[CH:11][CH:10]=2)=[O:38])[CH:20]=[CH:19]3)[CH:29]=[CH:28][C:27]=1[CH3:30])=[O:37]