Sodium hydride → HCID 58679245, compound

HRID 18930Notes

Reaction equation

[OH:1][CH2:2][C:3]([N:5]1[CH2:10][CH2:9][NH:8][C:7](=[O:11])[C:6]1([CH3:13])[CH3:12])=[O:4].[H-].[Na+].CC1C=CC(S(O[C:27](=[CH:32][C:33]#[N:34])[C:28]([F:31])([F:30])[F:29])(=O)=O)=CC=1>CN(C=O)C>[NH2:34][C:33]1[CH:32]=[C:27]([C:28]([F:31])([F:30])[F:29])[O:1][C:2]=1[C:3]([N:5]1[CH2:10][CH2:9][NH:8][C:7](=[O:11])[C:6]1([CH3:13])[CH3:12])=[O:4]

Participants

Conditions

Temperature: 25 °C

Procedure

4-(2-Hydroxyacetyl)-3,3-dimethylpiperazin-2-one (0.090 g, 0.48 mmol) and sodium hydride (60%, 0.040 g, 0.97 mmol) were dissolved in 3 mL DMF and stirred at 25° C. for 30 min. To the resulting, cooled (0° C.) mixture was added drop-wise 3-cyano-1,1,1-trifluoroprop-2-en-2-yl 4-methylbenzenesulfonate (0.16 g, 0.56 mmol). The reaction was gradually warmed up to 25° C., stirred for an additional 2 hours, 2 additional equivalents of sodium hydride were added and the mixture stirred for another additional 4 hours. The reaction mixture was quenched with water, extracted with ethyl acetate, the combined organic layers dried, the solvent eliminated under vacuum and the crude product purified by preparative thin layer chromatography. (silicagel, dichloromethane:methanol 95:5) to afford 0.010 g of 4-(4-amino-2-(trifluoromethyl)furan-5-carbonyl)-3,3-dimethylpiperazin-2-one.

Workup

temperatureTo the resulting, cooled (0° C.) mixture
temperatureThe reaction was gradually warmed up to 25° C.
stirringstirred for an additional 2 hours
stirringthe mixture stirred for another additional 4 hours
customThe reaction mixture was quenched with water
extractionextracted with ethyl acetate
customthe combined organic layers dried
customthe crude product purified by preparative thin layer chromatography

Sources & evidence

ORD record: ord-b69304818b654a5384e7ee0d7462af51
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741479B2

Reaction notes

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