Oxalyl chloride → HCID 71765285, compound

HRID 1775360Notes

Reaction equation

HRID 1775360 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.[CH3:16][N:17]([CH3:32])[C:18]([C:20]1[CH:21]=[N:22][C:23]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:24][CH:25]=1)=[O:19].CCN(C(C)C)C(C)C>ClCCl.CN(C=O)C>[CH3:16][N:17]([CH3:32])[C:18]([C:20]1[CH:21]=[N:22][C:23]([N:26]2[CH2:31][CH2:30][N:29]([C:5](=[O:6])/[CH:4]=[CH:3]/[C:2]([F:9])([F:8])[F:1])[CH2:28][CH2:27]2)=[CH:24][CH:25]=1)=[O:19]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 57096144,4,4-Trifluorocrotonic acidHCID 79016966HCID 79016966, compound

Product 1

HCID 71765285HCID 71765285, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

(E)-4,4,4-Trifluorobut-2-enoic acid (32 mg, 0.23 mmol) was dissolved in dichloromethane (1 ml), oxalyl chloride (20 μl, 0.23 mol) 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 N,N-dimethyl-6-piperazin-1-yl-pyridine-3-carboxamide (35 mg, 0.15 mmol) and DIPEA (80 μl, 0.5 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 39 mg of a solid (0.11 mmol, yield 48%).

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-20b916f476b642139f4d7be7c3b86a10
Source dataset
uspto-grants-2016_02
Patent number
US09260441B2

Reaction notes

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