Triethylamine → HCID 57867428, compound
Reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(N(CC)CC)C.CN1CCCC1=O.[C:25](Cl)(=O)[C:26]([CH3:29])([CH3:28])[CH3:27]>CN(C)C1C=CN=CC=1.O>[C:26]([C:29]1[O:5][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[N:10][C:2]=2[N:1]=1)([CH3:28])([CH3:27])[CH3:25]Participants
Procedure
To a mixture of 2-aminonicotinic acid (13.8 g, 100 mmol), 4-dimethylaminopyridine (1.2 g, 10 mmol), triethylamine (55.8 mL, 400 mmol) and N-methylpyrrolidone (140 mL, 42 mmol) was added pivaloyl chloride (24.1 g, 200 mmol) dropwise at 0° C., and after the drop wise addition was finished, which was stirred overnight at room temperature. To the reaction mixture was added water, extracted with toluene, and the organic layer was washed with water and saturated sodium chloride water. After the solution was dried over anhydrous magnesium sulfate and filtered, the solvent was evaporated under a reduced pressure. To the residue was added n-heptane, which was suspended and stirred at 0° C., which was filtered to obtain the title compound (16.6 g).
Workup
- additionafter the drop wise addition
- extractionextracted with toluene
- washthe organic layer was washed with water and saturated sodium chloride water
- dry with materialAfter the solution was dried over anhydrous magnesium sulfate
- filtrationfiltered
- customthe solvent was evaporated under a reduced pressure
- additionTo the residue was added n-heptane, which
- stirringstirred at 0° C.
- filtrationwhich was filtered
Sources & evidence
- ORD record
- ord-baac0cd45b4648a48928ad35da964355
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513287B2
Reaction notes
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