HRID1257580

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID81531

Diisopropylethylamine

C8H19N

HCID23068067

tert-Butyl 3-aminoazepane-1-carboxylate

C11H22N2O2

结构：O=[N+]([O-])c1cnc2c(ccn2S(=O)(=O)c2ccccc2)c1Cl

HCID58394774

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)N1CCCCC(Nc2c([N+](=O)[O-])cnc3c2ccn3S(=O)(=O)c2ccccc2)C1

HCID67341246

未命名化合物

收率 83.2%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID3776

Isopropanol

C3H8O

CONDITIONS

反应条件

温度: 120 °C

PROCEDURE

实验过程

A mixture of 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (0.6981 g, 2.067 mmol), 3-Amino-azepane-1-carboxylic acid tert-butyl ester (0.4752 g, 2.217 mmol), and diisopropylethylamine (0.50 mL, 2.9 mmol) in propan-2-ol (12 mL) was heated in a microwave reactor at 120° C. for 20 minutes. The solvent was evaporated in vacuo and then purified by column chromatography on silica gel (gradient: 0 to 30% ethyl acetate in heptanes) affording 0.8869 g (83%) of 3-(1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-azepane-1-carboxylic acid tert-butyl ester. LCMS (Method E, ESI): RT=2.07 min, m+H=516.2.

WORKUP

后处理

customThe solvent was evaporated in vacuo
custompurified by column chromatography on silica gel (gradient: 0 to 30% ethyl acetate in heptanes)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ac71e6f8eec94344bd023f08be948d30
来源数据集: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08461328B2
来源说明: uspto-grants-2013_06

反应 SMILES

[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[C:18](Cl)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]([O:27][C:28]([N:30]1[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]([NH2:37])[CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].C(N(C(C)C)CC)(C)C>CC(O)C>[C:23]([O:27][C:28]([N:30]1[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]([NH:37][C:18]2[C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=[C:14]3[N:10]([S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])[CH:11]=[CH:12][C:13]=23)[CH2:31]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]