HRID1458419

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6228

N,N-Dimethylformamide

C3H7NO

HCID8857

Ethyl acetate

C4H8O2

HCID24758

Sodium hydride

HNa

HCID9837748

2-Naphthalenecarbonitrile, 7-(bromomethyl)-

C12H8BrN

结构：COC(=O)c1cc(N(C(=O)OC(C)(C)C)C2CCNCC2)cc2nc(C(C)C)[nH]c12

HCID178498449

未命名化合物

PRODUCTS

生成物

结构：COC(=O)c1cc(N(C(=O)OC(C)(C)C)C2CCNCC2)cc2nc(C(C)C)n(Cc3ccc(C#N)c4ccccc34)c12

HCID22100849

未命名化合物

结构：COC(=O)c1cc(N(C(=O)OC(C)(C)C)C2CCNCC2)cc2c1nc(C(C)C)n2Cc1ccc(C#N)c2ccccc12

HCID54030373

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

PROCEDURE

实验过程

To 2-isopropyl-4-methoxycarbonyl-6-(N-(tert-butoxycarbonyl)piperidin-4-ylamino)benzimidazole (3.3 g) in DMF (200 mL) was added NaH (0.35 g) at ambient temperature. After stirring at ambient temperature for 30 minutes, the reaction flask was cooled to -10° C. and 7-bromomethyl-2-naphthonitrile (2.2 g) was added. The reaction was allowed to warm to ambient temperature and stirred at ambient temperature for 15 hours. The reaction was worked up between ethyl acetate and H2O. The organic layer was dried, concentrated and purified by silica gel chromatography (hexane/ethyl acetate/CH2Cl2 /methanol, gradient) to afford 1-(4-cyanonaphth-1-yl)methyl-2-isopropyl-4-methoxycarbonyl-6-(N-(tert-butoxycarbonyl)piperidin-4-ylamino)benzimidazole, and 1-(4-cyanonaphth-1-yl)methyl-2-isopropyl-7-methoxycarbonyl-5-(N-(tert-butoxycarbonyl)-piperidin-4-ylamino)benzimidazole.

WORKUP

后处理

temperaturethe reaction flask was cooled to -10° C.
temperatureto warm to ambient temperature
stirringstirred at ambient temperature for 15 hours
customThe organic layer was dried
concentrationconcentrated
custompurified by silica gel chromatography (hexane/ethyl acetate/CH2Cl2 /methanol, gradient)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ea350aa2182e49299acdeb8144e442db
来源数据集: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05849759
来源说明: uspto-grants-1998_12

反应 SMILES

[CH:1]([C:4]1[NH:5][C:6]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([N:17]([CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:9][C:7]=2[N:8]=1)([CH3:3])[CH3:2].[H-].[Na+].BrC[C:35]1[CH:44]=[C:43]2[C:38]([CH:39]=[CH:40][C:41](C#N)=[CH:42]2)=[CH:37][CH:36]=1.[C:47](O[CH2:51][CH3:52])(=O)C.[CH3:53][N:54]([CH:56]=O)C>O>[C:53]([C:39]1[C:38]2[C:43](=[CH:44][CH:35]=[CH:36][CH:37]=2)[C:42]([CH2:47][N:8]2[C:7]3[CH:9]=[C:10]([N:17]([CH:25]4[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]4)[C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[CH:11]=[C:12]([C:13]([O:15][CH3:16])=[O:14])[C:6]=3[N:5]=[C:4]2[CH:1]([CH3:3])[CH3:2])=[CH:41][CH:40]=1)#[N:54].[C:56]([C:39]1[C:38]2[C:37](=[CH:36][CH:35]=[CH:44][CH:43]=2)[C:51]([CH2:52][N:5]2[C:6]3[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([N:17]([CH:25]4[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]4)[C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])=[CH:9][C:7]=3[N:8]=[C:4]2[CH:1]([CH3:3])[CH3:2])=[CH:41][CH:40]=1)#[N:54]