Hydrochloric Acid → N-{3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-3-fluoromethylpyrazine-2-carboxamide

HRID 2388629Notes

Reaction equation

[F:1][CH2:2][C:3]1[C:4]([C:9]([O:11]C)=O)=[N:5][CH:6]=[CH:7][N:8]=1.[CH2:13]([C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[C:24]([O:33][CH3:34])([C:29]([F:32])([F:31])[F:30])[C:25]([F:28])([F:27])[F:26])[NH2:20])[CH:14]([CH3:16])[CH3:15].C[O-].[Na+].Cl>CO>[CH2:13]([C:17]1[CH:18]=[C:19]([NH:20][C:9]([C:4]2[C:3]([CH2:2][F:1])=[N:8][CH:7]=[CH:6][N:5]=2)=[O:11])[CH:21]=[CH:22][C:23]=1[C:24]([O:33][CH3:34])([C:25]([F:28])([F:26])[F:27])[C:29]([F:30])([F:31])[F:32])[CH:14]([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 60 °C

Procedure

Methyl 3-fluoromethylpyrazine-2-carboxylate (390 mg, 2.29 mmol) and 3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline (750 mg, 2.29 mmol) were stirred, followed by adding a 28% by weight methanol solution of sodium methoxide (4.4 g, 22.9 mmol), heating at 60° C. for 3 hours while stirring, pouring into a diluted HCl solution, extracting with ethyl acetate and washing with water. The reaction solution was dried over magnesium sulfate, and concentrated under reduced pressure, and then the residue was purified by using silica gel chromatography (hexane:ethyl acetate=3:1) to obtain 0.71 g of the desired compound.

Workup

extractionextracting with ethyl acetate
washwashing with water
dry with materialThe reaction solution was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customthe residue was purified

Sources & evidence

ORD record: ord-091b49a4710b47dcbc4bf5615ea1c066
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08269045B2

Reaction notes

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