1,2-Diaminocyclohexane, trans- → 7-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-2-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

HRID 80091Notes

Reaction equation

HRID 80091 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13].[C:14]([O:18][C:19]([N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28](Br)[CH:29]=2)[CH2:24][CH2:23][C:22]1=[O:32])=[O:20])([CH3:17])([CH3:16])[CH3:15].N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[C:14]([O:18][C:19]([N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([N:10]3[CH2:11][CH2:12][N:8]([C:3]4[CH:4]=[N:5][CH:6]=[CH:7][C:2]=4[CH3:1])[C:9]3=[O:13])[CH:29]=2)[CH2:24][CH2:23][C:22]1=[O:32])=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-oneHCID 687848337-bromo-2-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

Product 1

HCID 687853077-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-2-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl esterYield 67.48%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 14, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 0.15 g, 0.00084 mol) was reacted with 7-bromo-2-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (0.276 g 0.00084 mol), 1,4-dioxane (20 mL), copper iodide (0.0158 g, 0.000084 mol), trans-1.2-diamino cyclohexane (0.28 g, 0.00025 mol) and potassium phosphate (0.356 g, 0.00168 mol) to afford the crude product. Purification by column chromatography on silica gel (5% MeOH in CHCl3) afforded 0.145 g of 7-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-2-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (67.48% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (5% MeOH in CHCl3)

Sources & evidence

ORD record
ord-c532bf3529794989b2b4b82d5aa4d64c
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

Loading…