HRID1517080

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID2724141

Tetra-n-butylammonium fluoride

C16H36FN

结构：Cc1cc(-c2cccc(C(F)(F)F)c2)c(N(S(C)(=O)=O)S(C)(=O)=O)nc1C(=O)N1CCC(N2CCCC2)CC1

HCID57441126

未命名化合物

2 次

PRODUCTS

生成物

结构：Cc1cc(-c2cccc(C(F)(F)F)c2)c(NS(C)(=O)=O)nc1C(=O)N1CCC(N2CCCC2)CC1

HCID57441147

未命名化合物

收率 67.6%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

To a solution of 0.13 g (0.2 mmol) of N-{5-methyl-6-[(4-pyrrolidin-1-ylpiperidin-1-yl)carbonyl]-3-[3-(trifluoromethyl)phenyl]pyridin-2-yl}-N-(methylsulfonyl)methanesulfonamide (intermediate 4) in 2.0 ml of THF was added 0.2 ml (0.2 mmol) of a tetrabutylammonium fluoride solution (1M in THF) and the reaction mixture was subsequently heated up to reflux. After 4 days, the solvent was evaporated and the crude product purified by flash column chromatography (CH2Cl2/MeOH 98:2 to 4:1) to give 0.069 g (64%) of the title compound as yellow amorphous solid. MS: 511.3 (MH+).

WORKUP

后处理

temperaturethe reaction mixture was subsequently heated up
temperatureto reflux
customthe solvent was evaporated
customthe crude product purified by flash column chromatography (CH2Cl2/MeOH 98:2 to 4:1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-5d6fc428d65a482bb78d7233f9fbe682
来源数据集: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08227613B2
来源说明: uspto-grants-2012_07

反应 SMILES

[CH3:1][C:2]1[CH:3]=[C:4]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=2)[C:5]([N:21](S(C)(=O)=O)[S:22]([CH3:25])(=[O:24])=[O:23])=[N:6][C:7]=1[C:8]([N:10]1[CH2:15][CH2:14][CH:13]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:12][CH2:11]1)=[O:9].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:37])[F:38])[CH:31]=2)[C:5]([NH:21][S:22]([CH3:25])(=[O:23])=[O:24])=[N:6][C:7]=1[C:8]([N:10]1[CH2:11][CH2:12][CH:13]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:14][CH2:15]1)=[O:9]