HRID1685158

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10387

Benzyl chloroformate

C8H7ClO2

HCID81531

Diisopropylethylamine

C8H19N

结构：CC(C)(C)OC(=O)N1CCC(c2nc(-c3ccc(F)c(Cl)c3)cn2CCN)CC1

HCID67265114

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)N1CCC(c2nc(-c3ccc(F)c(Cl)c3)cn2CCNC(=O)OCc2ccccc2)CC1

HCID67265298

未命名化合物

收率 42.4%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

Dissolve 4-[1-(2-amino-ethyl)-4-(3-chloro-4-fluoro-phenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (0.94 mmol; 396.7 mg) in DCM (20 mL) and add DIPEA (1.41 mmol; 0.25 mL) and benzyl chloroformate (0.94 mmol; 0.14 mL). Stir 20 min and wash with saturated sodium bicarbonate, dry over MgSO4, filter and evaporate. Purify over 40 g silica gel with 0-40% EA/DCM to provide the title compound (222 mg; 42%). MS (ES): m/z=557 (M+H).

WORKUP

后处理

washwash with saturated sodium bicarbonate
dry with materialdry over MgSO4
filtrationfilter
customevaporate
customPurify over 40 g silica gel with 0-40% EA/DCM

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-1acf8dc4527e4d9dbe745148d1e43523
来源数据集: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08148387B2
来源说明: uspto-grants-2012_04

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:27][CH2:28][NH2:29])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([Cl:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.Cl[C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:27][CH2:28][NH:29][C:40]([O:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:41])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([Cl:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]