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 1168531Notes

Reaction equation

HRID 1168531 reaction equation
[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

Participants

6

Reactant 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

Product 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-carboxamideYield 57%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-60ce2db48a2e44359fa51128ebc7fc7c
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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