HRID1244011

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID4219896

N-Boc-2-isothiocyanatoethylamine

C8H14N2O2S

结构：COc1cc2c(cc1CN[C@H]1CCCN[C@H]1c1ccccc1)N(C)C(=O)CC2

HCID10309370

未命名化合物

PRODUCTS

生成物

结构：COc1cc2c(cc1CNC1CCCN(C(=S)NCCNC(=O)OC(C)(C)C)C1c1ccccc1)N(C)C(=O)CC2

HCID86587884

未命名化合物

收率 70%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID241

Benzene

C6H6

溶剂HCID3283

Diethyl Ether

C4H10O

PROCEDURE

实验过程

6-Methoxy-1-methyl-7-[(2S,3S)-(2-phenyl-piperidin-3-ylamino)-methyl]-3,4-dihydro-1H-quinolin-2-one (750 mg, 1.98 mmol) and N-BOC-2-isothiocyanatoethylamine (400 mg, 1.98 mmol) were stirred in 20 mL of benzene at room temperature for 16 hours. The reaction was diluted with diethyl ether and washed 1× with water, dried over MgSO4, filtered, and concentrated. Silica gel chromatography using (6:1 ethyl acetate/hexane) gave 800 mg (70% yield) of [2-({3-[(6-Methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-ylmethyl)-amino]-2-phenyl-piperidine-1-carbothioyl}-amino)-ethyl]-carbamic acid tert-butyl ester. Rf=0.11 (6:1 ethyl acetate/hexane).

WORKUP

后处理

washwashed 1× with water
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-2b9bb208f20c4ccdb2ed7b1d4d9bc8be
来源数据集: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07119207B2
来源说明: uspto-grants-2006_10

反应 SMILES

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH2:13][NH:14][C@H:15]1[CH2:20][CH2:19][CH2:18][NH:17][C@H:16]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[N:9]([CH3:27])[C:8](=[O:28])[CH2:7][CH2:6]2.[C:29]([NH:36][CH2:37][CH2:38][N:39]=[C:40]=[S:41])([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>C1C=CC=CC=1.C(OCC)C>[C:32]([O:31][C:29](=[O:30])[NH:36][CH2:37][CH2:38][NH:39][C:40]([N:17]1[CH2:18][CH2:19][CH2:20][CH:15]([NH:14][CH2:13][C:12]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][C:8](=[O:28])[N:9]3[CH3:27])=[CH:4][C:3]=2[O:2][CH3:1])[CH:16]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[S:41])([CH3:35])([CH3:33])[CH3:34]