HRID1882560

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID21978278

未命名化合物

2 次

结构：CC(C)(C)OC(=O)N[C@H]1C[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O

HCID66630888

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)N[C@H]1C[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NC4CCN(c5ccccn5)CC4)nc32)[C@H](O)[C@@H]1O

HCID24863127

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID3776

Isopropanol

C3H8O

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

To a suspension of {(1S,2R,3S,4R)-4-[2-(2-amino-ethylcarbamoyl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-carbamic acid tert-butyl ester (2.5 g, 4.05 mmol) in IPA (10 ml) is added imidazole-1-carboxylic acid (3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4-yl)-amide (Intermediate C) (151 ml of a 10 mg/ml solution in DCM, 5.56 mmol) and the reaction mixture is stirred at room temperature overnight. The solvent is removed in vacuo and the crude product is purified by chromatography on silica eluting with DCM/MeOH (25:1 increasing to 15:1). The resulting solid is further purified by dissolving in DCM and washing the solution with water, drying (MgSO4) and concentrating in vacuo to afford the title product. (MH+ 820.7)

WORKUP

后处理

customThe solvent is removed in vacuo
customthe crude product is purified by chromatography on silica eluting with DCM/MeOH (25:1 increasing to 15:1)
customThe resulting solid is further purified
dissolutionby dissolving in DCM
washwashing the solution with water
dry with materialdrying (MgSO4)
concentrationconcentrating in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-1edf16351f8a43d788d72acf3ec79e1e
来源数据集: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08318750B2
来源说明: uspto-grants-2012_11

反应 SMILES

[C:1]([O:5][C:6](=[O:45])[NH:7][C@H:8]1[CH2:12][C@@H:11]([N:13]2[CH:21]=[N:20][C:19]3[C:14]2=[N:15][C:16]([C:37](=[O:42])[NH:38][CH2:39][CH2:40][NH2:41])=[N:17][C:18]=3[NH:22][CH2:23][CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:10]([OH:43])[C@@H:9]1[OH:44])([CH3:4])([CH3:3])[CH3:2].[N:46]1([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][N:61]=2)[CH2:51][CH2:50][CH:49]([NH:52][C:53](N2C=CN=C2)=[O:54])[CH2:48][CH2:47]1>CC(O)C.C(Cl)Cl>[C:1]([O:5][C:6](=[O:45])[NH:7][C@H:8]1[CH2:12][C@@H:11]([N:13]2[CH:21]=[N:20][C:19]3[C:14]2=[N:15][C:16]([C:37](=[O:42])[NH:38][CH2:39][CH2:40][NH:41][C:53]([NH:52][CH:49]2[CH2:48][CH2:47][N:46]([C:60]4[CH:65]=[CH:64][CH:63]=[CH:62][N:61]=4)[CH2:51][CH2:50]2)=[O:54])=[N:17][C:18]=3[NH:22][CH2:23][CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:10]([OH:43])[C@@H:9]1[OH:44])([CH3:4])([CH3:2])[CH3:3]