Water → HCID 69108794, compound

HRID 1838262Notes

Reaction equation

[H-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C@H:16]([CH3:17])[CH2:15][N:14]([C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[O:19])[C@@H:13]([CH3:28])[CH2:12]2)=[CH:7][C:6]=1[C:29]([F:32])([F:31])[F:30])#[N:4].[CH3:33]I.O>CN(C=O)C>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C@H:16]([CH3:17])[CH2:15][N:14]([C:18]([N:20]([CH3:33])[C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[O:19])[C@@H:13]([CH3:28])[CH2:12]2)=[CH:7][C:6]=1[C:29]([F:31])([F:32])[F:30])#[N:4]

Participants

Conditions

Temperature: 50 °C

Procedure

A 69 mg portion of 60% sodium hydride was suspended in 6 ml of DMF, 660 mg of trans-4-(4-cyano-3-trifluoromethylphenyl)-4′-fluoro-2,5-dimethylpiperazine-1-carboxanilide synthesized in Example 1-1 was added to the suspension under ice-cooling, and then the mixture was stirred at 50° C. for 10 minutes. The reaction solution was ice-cooled, 0.11 ml of methyl iodide was added dropwise thereto, and then the mixture was stirred at room temperature for 2 hours. The reaction mixture was mixed with water, extracted with ethyl acetate, washed with saturated brine and then dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by a silica gel column chromatography to obtain 620 mg of the title compound from ethyl acetate-hexane eluate.

Workup

temperaturecooling
temperaturecooled
stirringthe mixture was stirred at room temperature for 2 hours
extractionextracted with ethyl acetate
washwashed with saturated brine
dry with materialdried over sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record: ord-681ef7cacce04baea1a715a4865a9554
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06673799B1

Reaction notes

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