Oxalyl chloride → (E)-4,4-Difluoro-N-[2-[(4-methylthiazol-2-yl)amino]ethyl]pent-2-enamide
Reaction equation
[F:1][C:2]([F:9])([CH3:8])/[CH:3]=[CH:4]/[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.Cl.[CH3:17][C:18]1[N:19]=[C:20]([NH:23][CH2:24][CH2:25][NH2:26])[S:21][CH:22]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[F:9][C:2]([F:1])([CH3:8])/[CH:3]=[CH:4]/[C:5]([NH:26][CH2:25][CH2:24][NH:23][C:20]1[S:21][CH:22]=[C:18]([CH3:17])[N:19]=1)=[O:7]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
(E)-4,4-Difluoropent-2-enoic acid (31 mg, 0.23 mmol) was dissolved in DCM (0.5 ml containing one drop of dimethyl formamide), oxalyl chloride was added (20 μl, 0.23 mmol) and the solution was stirred at room temperature for 15 minutes. This solution was added to a solution of N′-(4-methylthiazol-2-yl)ethane-1,2-diamine hydrochloride (24 mg, 0.15 mmol) and diisopropylethylamine (88 μl, 0.5 mmol) dissolved in DCM (2 ml) and the resulting mixture was stirred at room temperature for three hours. The volatiles were removed under reduced pressure and the residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and 10% to 100% acetonitrile) to yield 11 mg of a solid (0.04 mmol, 27%).
Workup
- stirringthe resulting mixture was stirred at room temperature for three hours
- customThe volatiles were removed under reduced pressure
- customthe residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and 10% to 100% acetonitrile)
Sources & evidence
- ORD record
- ord-36dec234ddf341869a50d75a00f71d2c
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321724B2
Reaction notes
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