Triethylamine → HCID 89825754, compound

HRID 1775330Notes

Reaction equation

HRID 1775330 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.Cl.[N:17]1([C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(N(CC)CC)C>ClCCl.CN(C=O)C.C(OC(=O)C)C>[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5]([N:20]1[CH2:21][CH2:22][N:17]([C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=2)[CH2:18][CH2:19]1)=[O:6]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57096144,4,4-Trifluorocrotonic acidHCID 529881592-(Piperazin-1-yl)quinoline hydrochloride

Product 1

HCID 89825754HCID 89825754, compoundYield 46%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(E)-4,4,4-Trifluorobut-2-enoic acid (28 mg, 0.2 mmol) was dissolved in dichloromethane (1 ml), oxalyl chloride (18 μl, 0.2 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 2-piperazin-1-ylquinoline hydrochloride (25 mg, 0.1 mmol) in DMF (0.5 ml). Triethylamine (42 μl, 0.3 mmol) was added and the resulting mixture was stirred at room temperature for two hours. The mixture was diluted with ethylacetate and the resulting mixture was washed with saturated sodium bicarbonate solution, brine and dried (MgSO4). The solvent was removed 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 15 mg of a solid (0.046 mmol, 46%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for two hours
  2. washthe resulting mixture was washed with saturated sodium bicarbonate solution, brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed under reduced pressure
  5. customthe resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and acetonitrile)

Sources & evidence

ORD record
ord-9dc72bb88a1c473395407ae666cf95e5
Source dataset
uspto-grants-2016_02
Patent number
US09260441B2

Reaction notes

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