Diisopropylethylamine → N,2,6-trimethyl-4-[4-[(E)-4,4,4-trifluorobut-2-enoyl]piperazin-1-yl]pyridine-3-carboxamide
Reaction equation
[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5](O)=[O:6].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:43][NH:44][C:45]([C:47]1[C:48]([CH3:60])=[N:49][C:50]([CH3:59])=[CH:51][C:52]=1[N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1)=[O:46]>CN(C=O)C>[CH3:43][NH:44][C:45]([C:47]1[C:48]([CH3:60])=[N:49][C:50]([CH3:59])=[CH:51][C:52]=1[N:53]1[CH2:58][CH2:57][N:56]([C:5](=[O:6])/[CH:4]=[CH:3]/[C:2]([F:9])([F:8])[F:1])[CH2:55][CH2:54]1)=[O:46]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
(E)-4,4,4-Trifluorobut-2-enoic acid (21 mg, 0.15 mmol) was dissolved in anhydrous DMF (1 ml), diisopropylethylamine (52 μl, 0.3 mmol) was added followed by HBTU (60 mg, 0.15 mmol) and the mixture was stirred at room temperature for 15 minutes. N,2,6-trimethyl-4-piperazin-1-yl-pyridine-3-carboxamide (37.2 mg, 0.15 mmol) was dissolved in a mixture of DMF (0.5 ml) and diisopropylethylamine (26 μl, 0.15 mmol) and the resulting solution was added to the solution of the activated carboxylic acid. The resulting mixture was stirred at room temperature for three hours, the solvent was removed under reduced pressure and the raw product was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile) to yield 21.4 mg of a solid (0.058 mmol, 38%).
Workup
- stirringThe resulting mixture was stirred at room temperature for three hours
- customthe solvent was removed under reduced pressure
- customthe raw product was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile)
Sources & evidence
- ORD record
- ord-da8c88080e1e4ecb9c1f83c0f938030d
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08883791B2
Reaction notes
Loading…