Triethylamine → 2-(8-Difluoromethylquinolin-5-yl)carbonyl-4,4,6,6-tetramethyl-cyclohexane-1,3,5-trione

HRID 1795748Notes

Reaction equation

[CH3:1][C:2]1([CH3:13])[C:7](=[O:8])[C:6]([CH3:10])([CH3:9])[C:5](=[O:11])[CH2:4][C:3]1=[O:12].[F:14][CH:15]([F:29])[C:16]1[C:25]2[N:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:19]([C:26](O)=[O:27])=[CH:18][CH:17]=1.C1(N=C=NC2CCCCC2)CCCCC1.C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C[Si](C#N)(C)C>[F:29][CH:15]([F:14])[C:16]1[CH:17]=[CH:18][C:19]([C:26]([CH:4]2[C:3](=[O:12])[C:2]([CH3:13])([CH3:1])[C:7](=[O:8])[C:6]([CH3:9])([CH3:10])[C:5]2=[O:11])=[O:27])=[C:20]2[C:25]=1[N:24]=[CH:23][CH:22]=[CH:21]2

Participants

Conditions

Temperature: 25 °C

Procedure

0.26 g (1.4 mmol) of 2,2,4,4-tetramethylcyclohexane-1,3,5-trione was dissolved in 10 ml of acetonitrile, 0.34 g (1.4 mmol) of 8-difluoromethyl-5-quinolinecarboxylic acid and 0.38 g (1.9 mmol) of dicyclohexylcarbodiimide were added and the mixture was stirred at 25° C. for 17 hours. 0.57 g (5.6 mmol) of triethylamine and 5 drops of trimethylsilyl cyanide were then added to the suspension, and stirring was continued at 25° C. for a further 25 hours. 50 ml of 5% strength potassium carbonate solution were subsequently added, the mixture was filtered, the filtrate was washed with methyl tert-butyl ether, the aqueous phase was adjusted to pH 2 using concentrated hydrochloric acid and the precipitate was filtered off, washed with water and dried. Yield: 0.25 g (colorless crystals);

Workup

stirringstirring
waitwas continued at 25° C. for a further 25 hours
filtrationthe mixture was filtered
washthe filtrate was washed with methyl tert-butyl ether
filtrationthe precipitate was filtered off
washwashed with water
customdried

Sources & evidence

ORD record: ord-00353705463d409ab1640af49d572961
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030063B1

Reaction notes

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