4-Chlorobenzylamine → HCID 12083065, compound

HRID 1168538Notes

Reaction equation

HRID 1168538 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9]3=[C:10]([C:12](=[O:18])[C:13]([C:15](O)=[O:16])=[CH:14][N:8]3[N:7]([CH3:19])[CH2:6][CH2:5]2)[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:15]([C:13]2[C:12](=[O:18])[C:10]3[CH:11]=[C:2]([I:1])[CH:3]=[C:4]4[C:9]=3[N:8]([CH:14]=2)[N:7]([CH3:19])[CH2:6][CH2:5]4)=[O:16])=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 660364-ChlorobenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 12083064HCID 12083064, compound

Product 1

HCID 12083065HCID 12083065, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-Iodo-1-methyl-7-oxo-2,3-dihydro-1H,7H-pyrido[3,2,1-ij]cinnoline-8-carboxylic acid (Preparation 39, 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 the title compound. Physical characteristics: 1H NMR (CDCl3) δ8.91, 8.70, 7.87, 7.32, 4.65, 3.51, 3.13, 2.90; MS (ESI+) m/z 494.0; HRMS (FAB) m/z 494.0142 (C20H17ClIN3O2+H); TLC (silica gel GF): Rf=0.27 EtOAc/CH2Cl2 (1/6).

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-7c31977d820f4a3eaba5b9660a15aafd
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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