HRID1804666

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：C#Cc1ccc2[nH]c([C@@H]3CCCCN3C(=O)OCc3ccccc3)nc2c1

HCID178435594

未命名化合物

PRODUCTS

生成物

结构：O=C(OCc1ccccc1)N1CCCC[C@H]1c1nc2cc(C#C/C=C/c3ccc4[nH]c([C@@H]5CCCCN5C(=O)OCc5ccccc5)nc4c3)ccc2[nH]1

HCID178525129

未命名化合物

收率 14.3%

AUXILIARIES

试剂、催化剂与溶剂

结构：Cc1ccc(C(C)C)cc1.Cc1ccc(C(C)C)cc1.[Cl][Ru][Cl].[Cl][Ru][Cl]

催化剂HCID10908223

未命名化合物

PROCEDURE

实验过程

A mixture of (S)-2-(5-ethynyl-1H-benzoimidazol-2-yl)-piperidine-1-carboxylic acid benzyl ester (41 mg, 0.115 mmol) and dichloro(p-cymene) ruthenium (II) dimer (5 mg) is purged with N2. AcOH (1 mL) is added and the mixture is stirred at room temperature overnight and concentrated in vacuum to dryness. The residue is purified by flash column chromatography on silica gel (EtOAc/hexanes 5% to 100%) and repurified by reverse phase HPLC using a gradient of CH3CN/water to afford the title compound (5.9 mg, 7%).

WORKUP

后处理

customis purged with N2
additionAcOH (1 mL) is added
concentrationconcentrated in vacuum to dryness
customThe residue is purified by flash column chromatography on silica gel (EtOAc/hexanes 5% to 100%)
customrepurified by reverse phase HPLC

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-5663bf47bbd3477193ebdff751b18458
来源数据集: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08354419B2
来源说明: uspto-grants-2013_01

反应 SMILES

[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24]([C:26]#[CH:27])=[CH:25][C:19]=2[N:18]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC1C=CC(C(C)C)=CC=1.CC1C=CC(C(C)C)=CC=1.Cl[Ru]Cl.Cl[Ru]Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24](/[CH:26]=[CH:27]/[C:27]#[C:26][C:24]3[CH:23]=[CH:22][C:20]4[NH:21][C:17]([C@@H:12]5[CH2:13][CH2:14][CH2:15][CH2:16][N:11]5[C:9]([O:8][CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)=[O:10])=[N:18][C:19]=4[CH:25]=3)=[CH:25][C:19]=2[N:18]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1