HRID2190178

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：C=C[C@@H](CN(c1nc2oc(-c3ccc(F)cc3)c(C(=O)NC)c2cc1C(=C)C)S(C)(=O)=O)OCc1ccccc1

HCID54575747

未命名化合物

PRODUCTS

生成物

结构：CNC(=O)c1c(-c2ccc(F)cc2)oc2nc3c(cc12)C(C)=C[C@H](OCc1ccccc1)CN3S(C)(=O)=O

HCID66664425

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

结构：Cc1cc(C)c(N2CCN(c3c(C)cc(C)cc3C)[C]2=[Ru]([Cl])([Cl])=[CH]c2ccccc2OC(C)C)c(C)c1

催化剂HCID11763533

[1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene](dichloro)({2-[(propan-2-yl)oxy]phenyl}methylidene)ruthenium

C31H38Cl2N2ORu

溶剂HCID1140

Toluene

C7H8

CONDITIONS

反应条件

温度: 100 °C

PROCEDURE

实验过程

To a solution of (S)-6-(N-(2-(benzyloxy)but-3-enyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methyl-5-(prop-1-en-2-yl)furo[2,3-b]pyridine-3-carboxamide (543 mg, 0.963 mmol) in toluene is added Hoveyda-Grubbs 2nd generation catalyst (6 mg, 0.0096 mmol), and the reaction mixture is heated to 100° C. for 18 h. After the reaction is judged complete by LCMS, the toluene is removed in vacuo, and the solid is triturated with methanol to afford (S)-7-Benzyloxy-2-(4-fluoro-phenyl)-9-methanesulfonyl-5-methyl-8,9-dihydro-7H-1-oxa-9,10-diaza-cyclohepta[f]indene-3-carboxylic acid methylamide that is taken directly to the next step.

WORKUP

后处理

customthe toluene is removed in vacuo
customthe solid is triturated with methanol

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-58d8854e7fa14ed5ac8d5b161c4dc1b1
来源数据集: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08324239B2
来源说明: uspto-grants-2012_12

反应 SMILES

[CH2:1]([O:8][C@@H:9]([CH:39]=C)[CH2:10][N:11]([C:16]1[N:21]=[C:20]2[O:22][C:23]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)=[C:24]([C:25]([NH:27][CH3:28])=[O:26])[C:19]2=[CH:18][C:17]=1[C:36]([CH3:38])=C)[S:12]([CH3:15])(=[O:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3OC(C)C)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1>[CH3:28][NH:27][C:25]([C:24]1[C:19]2[CH:18]=[C:17]3[C:36]([CH3:38])=[CH:39][C@H:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH2:10][N:11]([S:12]([CH3:15])(=[O:13])=[O:14])[C:16]3=[N:21][C:20]=2[O:22][C:23]=1[C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)=[O:26]