HRID2081101

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID700

Ethanolamine

C2H7NO

结构：CCOC(=O)c1cnc(N)c2c(COc3cc(-c4nnc(Cc5ccc(Cl)cc5)o4)ccc3C)csc12

HCID24810242

未命名化合物

PRODUCTS

生成物

结构：Cc1ccc(-c2nnc(Cc3ccc(Cl)cc3)o2)cc1OCc1csc2c(C(=O)NCCO)cnc(N)c12

HCID24810285

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID679

Dimethyl sulfoxide

C2H6OS

CONDITIONS

反应条件

温度: 160 °C

PROCEDURE

实验过程

A solution of 4-amino-3-{5-[5-(4-chloro-benzyl)-[1,3,4]oxadiazol-2-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (0.07 g, 0.13 mmol) (from Example 42 supra) in dimethylsulfoxide (0.5 mL) was treated with ethanolamine (1.5 mL) and heated at 160° C. for 2.8 hours in a microwave reactor. The reaction mixture was purified by C18 column chromatography and SFC column chromatography to give 4-amino-3-{5-[5-(4-chloro-benzyl)-[1,3,4]oxadiazol-2-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid (2-hydroxy-ethyl)-amide as a white powder. (Yield 8 mg, 11%).

WORKUP

后处理

customThe reaction mixture was purified by C18 column chromatography and SFC column chromatography

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-364c5131e09c44588f0b0d440e4c0b4b
来源数据集: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07932390B2
来源说明: uspto-grants-2011_04

反应 SMILES

C(O[C:4]([C:6]1[C:7]2[S:15][CH:14]=[C:13]([CH2:16][O:17][C:18]3[CH:23]=[C:22]([C:24]4[O:25][C:26]([CH2:29][C:30]5[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=5)=[N:27][N:28]=4)[CH:21]=[CH:20][C:19]=3[CH3:37])[C:8]=2[C:9]([NH2:12])=[N:10][CH:11]=1)=[O:5])C.[CH2:38]([CH2:40][NH2:41])[OH:39]>CS(C)=O>[OH:39][CH2:38][CH2:40][NH:41][C:4]([C:6]1[C:7]2[S:15][CH:14]=[C:13]([CH2:16][O:17][C:18]3[CH:23]=[C:22]([C:24]4[O:25][C:26]([CH2:29][C:30]5[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=5)=[N:27][N:28]=4)[CH:21]=[CH:20][C:19]=3[CH3:37])[C:8]=2[C:9]([NH2:12])=[N:10][CH:11]=1)=[O:5]