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4-Chlorobenzylamine → N-(4-Chlorobenzyl)-9-iodo-3-methyl-7-oxo-2,3-dihydro-7H-[1,3,4]oxadiazino[6,5,4-ij]quinoline-6-carboxamide

HRID 1168531
ノート
印刷プレビュー

反応式

HRID 1168531 の反応式
[I:1][C:2]1[CH:3]=[C:4]2[C:9]3=[C:10]([O:12][CH2:13][N:14]([CH3:15])[N:8]3[CH:7]=[C:6]([C:16]([OH:18])=O)[C:5]2=[O:19])[CH:11]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][NH2:38])=[CH:35][CH:34]=1>O1CCCC1.CCOCC>[Cl:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][NH:38][C:16]([C:6]2[C:5](=[O:19])[C:4]3[C:9]4=[C:10]([O:12][CH2:13][N:14]([CH3:15])[N:8]4[CH:7]=2)[CH:11]=[C:2]([I:1])[CH:3]=3)=[O:18])=[CH:35][CH:34]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 660364-ChlorobenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 120830559-Iodo-3-methyl-7-oxo-2,3-dihydro-7H-[1,3,4]oxadiazino[6,5,4-ij]quinoline-6-carboxylic acid

生成物 1

HCID 12083056N-(4-Chlorobenzyl)-9-iodo-3-methyl-7-oxo-2,3-dihydro-7H-[1,3,4]oxadiazino[6,5,4-ij]quinoline-6-carboxamide収率 57%

試薬・触媒・溶媒 2

HCID 3283
Diethyl Ether
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 9-iodo-3-methyl-7-oxo-2,3-dihydro-7H-[1,3,4]oxadiazino[6,5,4-ij]quinoline-6-carboxylic acid (Preparation 31, 0.900 g) in tetrahydrofuran (25 mL) is refluxed with 1,1′-carbonyldiimidazole (0.631 g) for 5 h. The reaction mixture is cooled to room temperature and treated with 4-chlorobenzylamine (0.828 g). The reaction mixture is diluted with ether (75 mL), filtered, and the filtrate is concentrated at reduced pressure. The crude product is purified by chromatography, using 75 g of silica gel packed and eluted with EtOAc/CH2Cl2/heptane (1/4/5), to afford a 57% yield of the title compound. Physical characteristics: 1H NMR (DMSO-d6) δ10.15, 8.67, 8.12, 7.75, 7.37, 5.29, 4.54, 2.98; MS (EI) m/z 495 (M+); HRMS (FAB) m/z 495.9935 (C19H15ClIN3O3+H). Anal. Found: C, 45.97; H, 3.14; N, 8.39.

後処理

  1. filtrationfiltered
  2. concentrationthe filtrate is concentrated at reduced pressure
  3. customThe crude product is purified by chromatography
  4. washeluted with EtOAc/CH2Cl2/heptane (1/4/5)

出典と根拠

ORDレコード
ord-60ce2db48a2e44359fa51128ebc7fc7c
出典データセット
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06624159B2

反応ノート

読み込み中…

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