HRID28499

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID21412

Butanenitrile, 4-bromo-

C4H6BrN

HCID81531

Diisopropylethylamine

C8H19N

结构：COc1cccc(-c2c(C)n(Cc3c(F)cccc3C(F)(F)F)c(=O)n(C[C@H](N)c3ccccc3)c2=O)c1F

HCID11421412

未命名化合物

PRODUCTS

生成物

结构：COc1cccc(-c2c(C)n(Cc3c(F)cccc3C(F)(F)F)c(=O)n(C[C@H](NCCCC#N)c3ccccc3)c2=O)c1F

HCID69189415

未命名化合物

收率 94%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6342

Acetonitrile

C2H3N

PROCEDURE

实验过程

Compound 1f (110 mg, 0.2 mmol) was dissolved in acetonitrile (5 mL) and diisopropylethyl amine (52 mg, 0.4 mmol) was added, followed by the addition of 4-bromobutyronitrile (90 mg, 0.6 mmol). The reaction mixture was refluxed for 16 hours. Volatiles were evaporated and the residue was purified by flash chromatography (silica, 5% MeOH/CH2Cl2) to give compound 3a (115 mg, 94%). MS (CI) m/z 613.3 (MH+).

WORKUP

后处理

temperatureThe reaction mixture was refluxed for 16 hours
customVolatiles were evaporated
customthe residue was purified by flash chromatography (silica, 5% MeOH/CH2Cl2)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-b86f9762f7644a4dbb9725fb0521d333
来源数据集: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07419983B2
来源说明: uspto-grants-2008_09

反应 SMILES

[NH2:1][C@H:2]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:3][N:4]1[C:9](=[O:10])[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[C:12]=2[F:19])=[C:7]([CH3:20])[N:6]([CH2:21][C:22]2[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:23]=2[F:32])[C:5]1=[O:33].C(N(C(C)C)CC)(C)C.Br[CH2:50][CH2:51][CH2:52][C:53]#[N:54]>C(#N)C>[C:53]([CH2:52][CH2:51][CH2:50][NH:1][C@H:2]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:3][N:4]1[C:9](=[O:10])[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[C:12]=2[F:19])=[C:7]([CH3:20])[N:6]([CH2:21][C:22]2[C:27]([C:28]([F:29])([F:31])[F:30])=[CH:26][CH:25]=[CH:24][C:23]=2[F:32])[C:5]1=[O:33])#[N:54]