HRID1048078

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID34677

2-Aminotetralin

C10H13N

HCID65578

Ethanedioyl dichloride

C2Cl2O2

HCID81531

Diisopropylethylamine

C8H19N

结构：COC(=O)C1CCOc2cc(Oc3ccc(C(=O)O)cc3)c(C#N)cc21

HCID46221108

未命名化合物

PRODUCTS

生成物

结构：COC(=O)C1CCOc2cc(Oc3ccc(C(=O)NC4CCc5ccccc5C4)cc3)c(C#N)cc21

HCID67081013

未命名化合物

收率 74%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID6228

N,N-Dimethylformamide

C3H7NO

溶剂HCID6344

Dichloromethane

CH2Cl2

2 次

PROCEDURE

实验过程

4-(6-Cyano-4-(methoxycarbonyl)chroman-7-yloxy)benzoic acid (Preparation 2) (10 mg, 0.028 mmol) was diluted with DCM (500 uL) followed by the addition of oxalyl chloride in DCM (2M) (0.017 ml, 0.034 mmol) and 1 drop of DMF. After stirring for 30 minutes, 1,2,3,4-tetrahydro-naphthalen-2-ylamine (8.3 mg, 0.057 mmol) and DIEA (0.020 mL, 0.11 mmol) were added. After stirring for 2 hours, the reaction was loaded directly onto a biotage 12i cartridge and eluted with 5% ethyl acetate/hexanes to 100% ethyl acetate to yield methyl 7-(4-((1,2,3,4-tetrahydronaphthalen-2-yl)carbamoyl)phenoxy)-6-cyanochroman-4-carboxylate (10 mg, 73% yield).

WORKUP

后处理

stirringAfter stirring for 2 hours
washeluted with 5% ethyl acetate/hexanes to 100% ethyl acetate

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-a4b72c90e831490792524635f4e8068f
来源数据集: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08569522B2
来源说明: uspto-grants-2013_10

反应 SMILES

[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:23]([O:25][CH3:26])=[O:24])#[N:2].C(Cl)(=O)C(Cl)=O.[CH2:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:36][CH2:35][CH:34]1[NH2:43].CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[CH2:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:36][CH2:35][CH:34]1[NH:43][C:18]([C:17]1[CH:16]=[CH:15][C:14]([O:13][C:12]2[CH:11]=[C:10]3[C:5]([CH:6]([C:23]([O:25][CH3:26])=[O:24])[CH2:7][CH2:8][O:9]3)=[CH:4][C:3]=2[C:1]#[N:2])=[CH:22][CH:21]=1)=[O:20]