HRID1094505

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID81560

Methanesulfonic acid, 1,1'-anhydride

C2H6O5S2

结构：Nc1nccc(Oc2ccc3c(C(=O)Nc4ccc(F)c(C(F)(F)F)c4)cccc3c2)n1

HCID16071550

未命名化合物

PRODUCTS

生成物

结构：CS(=O)(=O)Nc1nccc(Oc2ccc3c(C(=O)Nc4ccc(F)c(C(F)(F)F)c4)cccc3c2)n1

HCID23652864

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

溶剂HCID1049

Pyridine

C5H5N

溶剂HCID6344

Dichloromethane

CH2Cl2

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

378 mg (2.17 mMol) methansulfonic acid anhydride are added in 3 portions to a solution of 300 mg (0.68 mMol) 6-(2-amino-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide (Step 10.3) in 4.5 ml CH2Cl2 and 7.5 ml pyridine. After 20 h, the solution is diluted with EtOAc and water, the aq. phase separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; CH2Cl2/THF 50:1-9:1) gives the title compound: m.p.: 246° C.; MS: [M−1]=519.

WORKUP

后处理

customthe aq. phase separated off
extractionextracted twice with EtOAc
washThe organic layers are washed with water and brine
dry with materialdried (Na2SO4)
concentrationconcentrated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ae4692db7e8b4ddda29b2f5fcb60a318
来源数据集: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08133886B2
来源说明: uspto-grants-2012_03

反应 SMILES

[CH3:1][S:2]([O:5]S(C)(=O)=O)(=O)=[O:3].[F:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:30][C:31]4[CH:36]=[CH:35][N:34]=[C:33]([NH2:37])[N:32]=4)=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[O:19])=[CH:13][C:12]=1[C:38]([F:41])([F:40])[F:39]>C(Cl)Cl.N1C=CC=CC=1.CCOC(C)=O.O>[F:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:30][C:31]4[CH:36]=[CH:35][N:34]=[C:33]([NH:37][S:2]([CH3:1])(=[O:5])=[O:3])[N:32]=4)=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[O:19])=[CH:13][C:12]=1[C:38]([F:40])([F:39])[F:41]