HRID931806

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID33557

未命名化合物

结构：Cc1cc2nc(OS(=O)(=O)C(F)(F)F)ccc2c(-c2ccc(Cl)cc2)c1[C@@H](COC(=O)C(C)(C)C)OC(C)(C)C

HCID86691982

未命名化合物

2 次

PRODUCTS

生成物

结构：Cc1cc2c(ccc3nnnn32)c(-c2ccc(Cl)cc2)c1[C@@H](COC(=O)C(C)(C)C)OC(C)(C)C

HCID66633692

未命名化合物

收率 23.9%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

溶剂HCID8857

Ethyl acetate

C4H8O2

CONDITIONS

反应条件

温度: 90 °C

PROCEDURE

实验过程

The mixture of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate (compound of Example 26)(30 mg) and sodium azide (32 mg) in DMF (1 mL) was heated at 90° C. for 4 hours. The mixture was diluted with ethyl acetate, and washed with water and brine, and dried with sodium sulfate. Concentration and purification by flash column chromatography (hexanes/EtOAc) gave (S)-2-tert-butoxy-2-(6-(4-chlorophenyl)-8-methyltetrazolo[1,5-a]quinolin-7-yl)ethyl pivalate (5.9 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C27H32ClN4O3: 495.2. Found: 495.2.

WORKUP

后处理

washwashed with water and brine
dry with materialdried with sodium sulfate
concentrationConcentration and purification by flash column chromatography (hexanes/EtOAc)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-fe9b25fa661b446d8a1055109e13f3c9
来源数据集: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09296758B2
来源说明: uspto-grants-2016_03

反应 SMILES

[C:1]([O:7][CH2:8][C@@H:9]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[C:10]1[C:11]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15](OS(C(F)(F)F)(=O)=O)[CH:14]=[CH:13]2)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[N-:41]=[N+:42]=[N-:43].[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:7][CH2:8][C@@H:9]([O:36][C:37]([CH3:39])([CH3:40])[CH3:38])[C:10]1[C:11]([C:29]2[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]1[N:41]=[N:42][N:43]=[C:15]1[CH:14]=[CH:13]2)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]