Oxalyl chloride → (E)-N-[2-[(6-Amino-2-methylsulfanyl-pyrimidin-4-yl)amino]ethyl]-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.FC(F)(F)S(O)(=O)=O.[NH2:24][CH2:25][CH2:26][NH:27][C:28]1[N:33]=[C:32]([S:34][CH3:35])[N:31]=[C:30]([NH2:36])[CH:29]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C)C=O.C(OCC)(=O)C>[NH2:36][C:30]1[N:31]=[C:32]([S:34][CH3:35])[N:33]=[C:28]([NH:27][CH2:26][CH2:25][NH:24][C:5](=[O:6])/[CH:4]=[CH:3]/[C:2]([F:9])([F:8])[F:1])[CH:29]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
(E)-4,4,4-Trifluorobut-2-enoic acid (21 mg, 0.15 mmol) was dissolved in DCM (1 ml containing one drop of DMF), oxalyl chloride was added (13 μl, 0.15 mmol) and the solution was stirred at room temperature for 15 minutes. This solution was added to a solution of N6-(2-Aminoethyl)-2-methylsulfanyl-pyrimidine-4,6-diamine trifluoromethanesulfonate (20 mg, 0.057 mmol) and diisopropylethylamine (51 μl, 0.3 mmol) dissolved in dimethylformamide (1 ml) and the resulting mixture was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate, washed with water and saturated sodium bicarbonate solution, dried over magnesium sulfate, the solvent was removed under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 3.3 mg of a white solid (0.001 mmol, 18%).
Workup
- stirringthe resulting mixture was stirred at room temperature for 2 hours
- washwashed with water and saturated sodium bicarbonate solution
- dry with materialdried over magnesium sulfate
- customthe solvent was removed under reduced pressure
- customThe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
Sources & evidence
- ORD record
- ord-b62f4f6e30a844efbe12c038e08a701e
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877934B2
Reaction notes
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