HRID558969

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID25517

未命名化合物

HCID33557

未命名化合物

结构：Cc1cc(C(=O)N2CCCCc3ccccc32)ccc1CNC(=O)N1CC(=O)N(CC#N)c2cccc(F)c21

HCID11584492

未命名化合物

PRODUCTS

生成物

结构：Cc1cc(C(=O)N2CCCCc3ccccc32)ccc1CNC(=O)N1CC(=O)N(Cc2nnn[nH]2)c2cccc(F)c21

HCID178426906

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度: 100 °C

PROCEDURE

实验过程

Sodium azide (78 mg, 1.2 mmol) and ammonium chloride (21 mg, 0.40 mmol) were added to a solution of 4-cyanomethyl-8-fluoro-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 2-methyl-4-(2,3,4,5-tetrahydrobenzo[b]azepine-1-carbonyl)benzylamide from Example 13 (210 mg, 0.40 mmol) in DMF (5 ml) and the mixture was stirred at 100° C. for 18 h. The mixture was cooled and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant CHCl3 100% to CHCl3:methanol;triethylamine 97:2:1 to CHCl3:methanol;triethylamine 94:4:2). The product was partitioned between chloroform and potassium hydrogen sulphate, separated and the organic phase was dried and evaporated in vacuo; yield 33 mg, 15%.

WORKUP

后处理

temperatureThe mixture was cooled
customevaporated in vacuo
customThe residue was purified by flash chromatography on silica (eluant CHCl3 100% to CHCl3:methanol;triethylamine 97:2:1 to CHCl3:methanol;triethylamine 94:4:2)
customThe product was partitioned between chloroform and potassium hydrogen sulphate
customseparated
customthe organic phase was dried
customevaporated in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-8f6b48b1178a430aaba52428b526211f
来源数据集: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08063038B2
来源说明: uspto-grants-2011_11

反应 SMILES

[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH4+].[CH3:7][C:8]1[CH:32]=[C:31]([C:33]([N:35]2[CH2:41][CH2:40][CH2:39][CH2:38][C:37]3[CH:42]=[CH:43][CH:44]=[CH:45][C:36]2=3)=[O:34])[CH:30]=[CH:29][C:9]=1[CH2:10][NH:11][C:12]([N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[F:24])[N:17]([CH2:25][C:26]#[N:27])[C:16](=[O:28])[CH2:15]1)=[O:13]>CN(C=O)C>[CH3:7][C:8]1[CH:32]=[C:31]([C:33]([N:35]2[CH2:41][CH2:40][CH2:39][CH2:38][C:37]3[CH:42]=[CH:43][CH:44]=[CH:45][C:36]2=3)=[O:34])[CH:30]=[CH:29][C:9]=1[CH2:10][NH:11][C:12]([N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[F:24])[N:17]([CH2:25][C:26]2[NH:27][N:3]=[N:2][N:1]=2)[C:16](=[O:28])[CH2:15]1)=[O:13]