Potassium Carbonate → N-[(4-chlorophenyl)methyl]-1-(2-diethylaminoethyl)-6-(3-hydroxyprop-1-ynyl)-4-oxo-quinoline-3-carboxamide

HRID 1067965Notes

Reaction equation

[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([C:21]#[C:22][CH2:23][OH:24])=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br.Br[CH2:35][CH2:36][N:37]([CH2:40][CH3:41])[CH2:38][CH3:39]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:21]#[C:22][CH2:23][OH:24])[CH:17]=3)[N:12]([CH2:35][CH2:36][N:37]([CH2:40][CH3:41])[CH2:38][CH3:39])[CH:11]=2)=[O:9])=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide from Preparation No. 5 (0.616 g) is dissolved in DMF (4 mL), and K2CO3 (0.93 g, 6.72 mmol) and 2-bromo-N,N-diethylethylamine hydrobromide (0.88 g, 3.35 mmol) are added. The reaction mixture is heated to 90° C. for 16. The mixture is partitioned between CHCl3 and water. The organic layer is concentrated in vacuo to give an oil. Column chromatography (elution with 1-5% MeOH/CHCl3) gave 0.10 g of a brown oil. Crystallization from ethyl acetate/hexane gave 0.013 g of the title compound as a solid.

Workup

customThe mixture is partitioned between CHCl3 and water
concentrationThe organic layer is concentrated in vacuo
customto give an oil
washColumn chromatography (elution with 1-5% MeOH/CHCl3)

Sources & evidence

ORD record: ord-8b1188b933ae4a39988b016a047b5f2e
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248739B1

Reaction notes

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