Ethyl Acetate → 7-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-3,4-dihydro-1H-quinolin-2-one

HRID 80092Notes

Reaction equation

HRID 80092 reaction equation
Cl.O1CCOCC1.C(OC([N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([N:25]3[CH2:29][CH2:28][N:27]([C:30]4[CH:31]=[N:32][CH:33]=[CH:34][C:35]=4[CH3:36])[C:26]3=[O:37])[CH:23]=2)[CH2:18][CH2:17][C:16]1=[O:38])=O)(C)(C)C.C(OC(=O)C)C>CCCCCC>[CH3:36][C:35]1[CH:34]=[CH:33][N:32]=[CH:31][C:30]=1[N:27]1[CH2:28][CH2:29][N:25]([C:22]2[CH:23]=[C:24]3[C:19]([CH2:18][CH2:17][C:16](=[O:38])[NH:15]3)=[CH:20][CH:21]=2)[C:26]1=[O:37]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 204431481,4-Dioxane hydrochlorideHCID 687853077-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-2-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

Product 1

HCID 687868967-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-3,4-dihydro-1H-quinolin-2-oneYield 43.8%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Dioxane hydrochloride (3 mL) was added to 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 (0.145 g, 0.00034 mol) at 0° C. The resulting reaction mixture was stirred at room temperature for 2 hours. The reaction was monitored by TLC (40% ethylacetate in hexane). Purification by preparative HPLC, followed by column chromatography on silica gel (5% MeOH in CHCl3) afforded 48 mg of the product (35.47% yield).

Workup

  1. customThe resulting reaction mixture
  2. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-32e4b2db6aa7414fa4b055e90e801e01
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

Loading…