Oxalyl chloride → (E)-N-[2-[(5-Ethyl-6-methyl-pyrimidin-4-yl)amino]butyl]-4,4,4-trifluoro-but-2-enamide
Reaction equation
[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5](O)=[O:6].C(Cl)(=O)C(Cl)=O.[CH2:16]([C:18]1[C:19]([NH:25][CH:26]([CH2:29][CH3:30])[CH2:27][NH2:28])=[N:20][CH:21]=[N:22][C:23]=1[CH3:24])[CH3:17].C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C=O)C>[CH2:16]([C:18]1[C:19]([NH:25][CH:26]([CH2:29][CH3:30])[CH2:27][NH:28][C:5](=[O:6])/[CH:4]=[CH:3]/[C:2]([F:9])([F:8])[F:1])=[N:20][CH:21]=[N:22][C:23]=1[CH3:24])[CH3:17]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
(E)-4,4,4-Trifluorobut-2-enoic acid (15 mg, 0.11 mmol) was dissolved in DCM (1 ml containing one drop of dimethyl formamide), oxalyl chloride was added (9.5 μl, 0.11 mmol) and the solution was stirred at room temperature for 15 minutes. This solution was added to a solution of N2-(5-Ethyl-6-methyl-pyrimidin-4-yl)butane-1,2-diamine (24.5 mg, 0.1 mmol) and diisopropylethylamine (44 μl, 0.25 mmol) dissolved in DMF (1 ml) and the resulting mixture was stirred at room temperature overnight. The volatiles were removed under reduced pressure and the residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 12.7 mg (0.038 mmol, 38%).
Workup
- stirringthe resulting mixture was stirred at room temperature overnight
- customThe volatiles were removed under reduced pressure
- customthe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
- customto yield 12.7 mg (0.038 mmol, 38%)
Sources & evidence
- ORD record
- ord-9508645282fe42af965a655f90344ab6
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877934B2
Reaction notes
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