HRID2371118

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID2734632

3-Chloro-4-fluorophenyl isocyanate

C7H3ClFNO

2 次

结构：CS(=O)(=O)c1ccc(CCCN2CCC[C@@H](CN3CCNCC3)C2)cc1

HCID57656734

未命名化合物

PRODUCTS

生成物

结构：CS(=O)(=O)c1ccc(CCCN2CCC[C@@H](CN3CCN(C(=O)Nc4ccc(F)c(Cl)c4)CC3)C2)cc1

HCID57656769

未命名化合物

收率 50%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID1140

Toluene

C7H8

PROCEDURE

实验过程

To a solution of 1-[((3R)-1-{3-[4-(methylsulfonyl)phenyl]propyl}piperidin-3-yl)methyl]piperazine (215 mg, 0.57 mmol) in toluene (15 ml) was added 3-chloro-4-fluorophenyl isocyanate (107 mg, 0.62 mmol) and the solution stirred for 18 hours. A further portion of 3-chloro-4-fluorophenyl isocyanate (54.0 mg, 0.31 mmol) was added and stirred for 30 minutes. The reaction was evaporated to an oil and flash column chromatography (silica, CH2Cl2 to 10% MeOH/CH2Cl2) gave N-(3-chloro-4-fluorophenyl)-4-[((3R)-1-{3-[4-(methylsulfonyl)phenyl]propyl}piperidin-3-yl)methyl]piperazine-1-carboxamide as a white foam (155 mg, 50%).

WORKUP

后处理

stirringstirred for 30 minutes
customThe reaction was evaporated to an oil and flash column chromatography (silica, CH2Cl2 to 10% MeOH/CH2Cl2)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-a175842ffb1540f5ab5f9d1f25ae51d4
来源数据集: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08710224B2
来源说明: uspto-grants-2014_04

反应 SMILES

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][C@@H:16]([CH2:20][N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[CH2:15]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Cl:27][C:28]1[CH:29]=[C:30]([N:35]=[C:36]=[O:37])[CH:31]=[CH:32][C:33]=1[F:34]>C1(C)C=CC=CC=1>[Cl:27][C:28]1[CH:29]=[C:30]([NH:35][C:36]([N:24]2[CH2:25][CH2:26][N:21]([CH2:20][C@@H:16]3[CH2:17][CH2:18][CH2:19][N:14]([CH2:13][CH2:12][CH2:11][C:8]4[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=4)[CH2:15]3)[CH2:22][CH2:23]2)=[O:37])[CH:31]=[CH:32][C:33]=1[F:34]