Oxalyl chloride → HCID 71765322, compound

HRID 1775362Notes

Reaction equation

HRID 1775362 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.[N:16]1([C:22]2[CH:27]=[C:26]([C:28](=[O:30])[CH3:29])[CH:25]=[CH:24][N:23]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.CCN(C(C)C)C(C)C>ClCCl.CN(C=O)C>[C:28]([C:26]1[CH:25]=[CH:24][N:23]=[C:22]([N:16]2[CH2:17][CH2:18][N:19]([C:5](=[O:6])/[CH:4]=[CH:3]/[C:2]([F:9])([F:8])[F:1])[CH2:20][CH2:21]2)[CH:27]=1)(=[O:30])[CH3:29]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 57096144,4,4-Trifluorocrotonic acidHCID 20785294HCID 20785294, compound

Product 1

HCID 71765322HCID 71765322, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

(E)-4,4,4-Trifluorobut-2-enoic acid (34 mg, 0.24 mmol) was dissolved in dichloromethane (1 ml), oxalyl chloride (21 μl, 0.24 mmol) and one drop of DMF were added and the resulting solution was stirred at room temperature for 10 minutes. This solution was added to a solution of 1-(2-piperazin-1-yl-4-pyridyl)ethanone (41 mg, 0.2 mmol) and DIPEA (105 μl, 0.6 mmol) in anhydrous DCM (2 ml) and the resulting mixture was stirred at room temperature overnight. The mixture was concentrated under reduced pressure and the resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and acetonitrile) to yield 37 mg of a solid (0.108 mmol, yield 47%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and acetonitrile)

Sources & evidence

ORD record
ord-f9315279fdf04a5d858c14e3c548f3ee
Source dataset
uspto-grants-2016_02
Patent number
US09260441B2

Reaction notes

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