HRID57758

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID1049

Pyridine

C5H5N

HCID31297

Methanesulfonyl chloride

CH3ClO2S

结构：CNC(=O)c1c(-c2ccc(F)cc2)oc2cc(N)c(-c3cc(N)cc(C(=O)NC(C)(C)C)c3)cc12

HCID90280652

未命名化合物

PRODUCTS

生成物

结构：CNC(=O)c1c(-c2ccc(F)cc2)oc2cc(NS(C)(=O)=O)c(-c3cc(NS(C)(=O)=O)cc(C(=O)NC(C)(C)C)c3)cc12

HCID90280520

未命名化合物

收率 69.2%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

To a solution of 6-amino-5-(3-amino-5-(tert-butylcarbamoyl)phenyl)-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (100 mg) and pyridine (0.170 mL) in CH2Cl2 (10 mL) was added methanesulfonyl chloride (72.4 mg) slowly at 0° C. The mixture was stirred at room temperature for 16 hours. The reaction was quenched with aqueous NaHCO3 and extracted with CH2Cl2. The organic layer was concentrated and the residue was purified by preparative HPLC to give 5-(3-(tert-butylcarbamoyl)-5-(methylsulfonamido)phenyl)-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide 4 (92 mg).

WORKUP

后处理

customThe reaction was quenched with aqueous NaHCO3
extractionextracted with CH2Cl2
concentrationThe organic layer was concentrated
customthe residue was purified by preparative HPLC

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-9c62f736f28049e486607ffc4ff12fd7
来源数据集: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09434738B2
来源说明: uspto-grants-2016_09

反应 SMILES

[NH2:1][C:2]1[C:21]([C:22]2[CH:27]=[C:26]([C:28](=[O:34])[NH:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH:25]=[C:24]([NH2:35])[CH:23]=2)=[CH:20][C:5]2[C:6]([C:16]([NH:18][CH3:19])=[O:17])=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1.N1C=CC=CC=1.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>C(Cl)Cl>[C:30]([NH:29][C:28]([C:26]1[CH:27]=[C:22]([C:21]2[C:2]([NH:1][S:43]([CH3:42])(=[O:45])=[O:44])=[CH:3][C:4]3[O:8][C:7]([C:9]4[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=4)=[C:6]([C:16]([NH:18][CH3:19])=[O:17])[C:5]=3[CH:20]=2)[CH:23]=[C:24]([NH:35][S:43]([CH3:42])(=[O:45])=[O:44])[CH:25]=1)=[O:34])([CH3:31])([CH3:32])[CH3:33]