N-methyl-2-pyrrolidone → Methyl 6-t-butylamino-5-fluoro-2-(1,1,3,3-tetramethylbutylamino)nicotinate

HRID 368466Notes

Reaction equation

CN1CCCC1=O.[C:8]([NH:12][C:13]1[C:22]([F:23])=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15](F)[N:14]=1)([CH3:11])([CH3:10])[CH3:9].[CH3:25][C:26]([NH2:33])([CH3:32])[CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29]>C(Cl)(Cl)Cl>[C:8]([NH:12][C:13]1[C:22]([F:23])=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([NH:33][C:26]([CH3:32])([CH3:25])[CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[N:14]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 140 °C

Procedure

To 7 ml N-methylpyrrolidone were added 2.44 g of methyl 6-t-butylamino-2,5-difluoronicotinate and 4.0 g of 1,1,3,3-tetramethylbutylamine, and the mixture was stirred at 140° C. for 16 hours and allowed to cool. After adding 50 ml of chloroform, the mixture was washed three times with 300 ml of distilled water. The chloroform layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The brown oily residue was subjected to column chromatography (silica gel, 40 g; eluent: chloroform:n-hexane, 1:1) to obtain 2.90 g of the title compound as a colorless oily residue.

Workup

temperatureto cool
washthe mixture was washed three times with 300 ml of distilled water
dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3602d271549c477aa9d0529fa7d072fe
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133284

Reaction notes

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