Diisopropylethylamine → (5S)-5-({[4-(4-fluorophenyl)piperidin-1-yl}sulfonyl]methyl)-5-methylimidazolidine-2,4-dione

HRID 2355153Notes

Reaction equation

Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[CH3:24][C@@:25]1([CH2:32][S:33](Cl)(=[O:35])=[O:34])[C:29](=[O:30])[NH:28][C:27](=[O:31])[NH:26]1>C1COCC1>[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:10][CH2:11][N:12]([S:33]([CH2:32][C@@:25]3([CH3:24])[NH:26][C:27](=[O:31])[NH:28][C:29]3=[O:30])(=[O:34])=[O:35])[CH2:13][CH2:14]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 50 °C

Procedure

4-(4-Fluorophenyl)piperidine hydrochloride (63 mg, 0.29 mmol) was taken up in 3 mL of dry THF, neutralized with diisopropylethylamine (50 μL, 0.29 mmol) and cooled on an ice-water bath. [(4S)-4-methyl-2,5-dioxo-imidazolodin-4-yl]methanesulfonyl chloride (80 mg, 0.35 mmol) was added and after stirring for 10 min, diisopropylethylamine (50 μL, 0.29 mmol) was added and the reaction mixture was stirred at ambient temperature until LC-MS (APCI) indicated consumption of the amine. The reaction mixture was evaporated and the residue taken up in EtOH and heated to 50° C. and allowed to cool before water was added. The precipitated product was collected and washed with EtOH/water and dried in vacuum to yield 87 mg.

Workup

temperaturecooled on an ice-water bath
stirringthe reaction mixture was stirred at ambient temperature until LC-MS (APCI)
customconsumption of the amine
customThe reaction mixture was evaporated
temperatureto cool before water
additionwas added
customThe precipitated product was collected
washwashed with EtOH/water
customdried in vacuum
customto yield 87 mg

Sources & evidence

ORD record: ord-d7eca5ecbe404b4c8add264ee9f843cd
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754750B2

Reaction notes

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