HRID638062

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6328

Methyl iodide

CH3I

HCID23665647

2-Methyl-2-propanol, potassium salt

C4H9KO

结构：NC(=O)c1cc(OCCNCC(O)COc2ccc(-c3nc(C(F)(F)F)c[nH]3)cc2)ccc1O

HCID178513694

未命名化合物

PRODUCTS

生成物

结构：Cn1cc(C(F)(F)F)nc1-c1ccc(OCC(O)CNCCOc2ccc(O)c(C(N)=O)c2)cc1

HCID2685

未命名化合物

结构：Cn1c(C(F)(F)F)cnc1-c1ccc(OCC(O)CNCCOc2ccc(O)c(C(N)=O)c2)cc1

HCID20255154

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

2 次

PROCEDURE

实验过程

0.48 g of potassium tert.-butoxide is added while stirring in an ice bath to a solution of 1 g of the 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-[4-(trifluoromethyl)-1H-imidazol-2-yl]-phenoxy]-2-propanol obtained according to Example 3 in 20 ml of dimethylformamide. After 10 minutes, a solution of 0.3 g of methyl iodide in 1 ml of dimethylformamide is added dropwise over a period of 20 minutes. The mixture is then stirred for 2 hours at room temperature, the solvent is removed in a rotary evaporator and the residue is chromatographed on silica gel with a solvent mixture of chloroform/methanol/ammonia (700:50:1), yielding the two isomeric compounds 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-[1-methyl-4-(trifluoromethyl)-1H-imidazol-2-yl]-phenoxy]-2-propanol having a melting point of 195°-197° and 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-[1-methyl-5-(trifluoromethyl)-1H-imidazol-2-yl]-phenoxy]-2-propanol having a melting point of 157°-159°.

WORKUP

后处理

customobtained
customthe solvent is removed in a rotary evaporator
customthe residue is chromatographed on silica gel with a solvent mixture of chloroform/methanol/ammonia (700:50:1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-cae42ef60d0b4c64be3d8aa4dae3865b
来源数据集: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04559354
来源说明: uspto-grants-1985_12

反应 SMILES

[CH3:1]C(C)([O-])C.[K+].[C:7]([C:10]1[CH:11]=[C:12]([CH:37]=[CH:38][C:39]=1[OH:40])[O:13][CH2:14][CH2:15][NH:16][CH2:17][CH:18]([OH:36])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[NH:28][CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[N:31]=2)=[CH:23][CH:22]=1)(=[O:9])[NH2:8].CI>CN(C)C=O>[C:7]([C:10]1[CH:11]=[C:12]([CH:37]=[CH:38][C:39]=1[OH:40])[O:13][CH2:14][CH2:15][NH:16][CH2:17][CH:18]([OH:36])[CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[N:28]([CH3:1])[CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[N:31]=2)=[CH:25][CH:26]=1)(=[O:9])[NH2:8].[C:7]([C:10]1[CH:11]=[C:12]([CH:37]=[CH:38][C:39]=1[OH:40])[O:13][CH2:14][CH2:15][NH:16][CH2:17][CH:18]([OH:36])[CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[N:31]([CH3:1])[C:30]([C:32]([F:35])([F:34])[F:33])=[CH:29][N:28]=2)=[CH:25][CH:26]=1)(=[O:9])[NH2:8]