Triethylamine → HCID 56949205, compound

HRID 333967

Reaction equation

HRID 333967 reaction equation
[C:1]([OH:10])(=O)/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(Cl)(=O)C(Cl)=O.[CH3:17][C:18]1[CH:27]=[C:26]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1.C(N(CC)CC)C>ClCCl.CN(C=O)C>[CH3:17][C:18]1[CH:27]=[C:26]([N:28]2[CH2:33][CH2:32][N:31]([C:1](=[O:10])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:30][CH2:29]2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 7023182-Methyl-4-(piperazin-1-yl)quinolineHCID 5282714trans-2-Octenoic acid

Product 1

HCID 56949205HCID 56949205, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent4×

Procedure

(E)-Oct-2-enoic acid (71.1 mg, 0.5 mmol) was dissolved in dichloromethane (1 ml) and a 2M solution of oxalyl chloride in dichloromethane was added (0.3 ml, 0.6 mmol). The solution was stirred at room temperature for one hour after which a drop of DMF was added. Stirring was continued for another hour, the mixture was evaporated to dryness under reduced pressure. The residue was dissolved in dichloromethane (1 ml), the resulting solution was added to a solution of 2-methyl-4-piperazin-1-yl-quinoline (103 mg, 0.45 mmol) and triethylamine (90 μl, 0.64 mmol) in dichloromethane (1 ml). The resulting mixture was stirred at room temperature overnight, diluted with dichloromethane (1 ml), washed with water and 2M NaOH (2 ml each) and evaporated to dryness under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile) to yield 121.3 mg of a solid (0.34 mmol, 77%).

Workup

  1. additionwas added
  2. waitwas continued for another hour
  3. customthe mixture was evaporated to dryness under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane (1 ml)
  5. stirringThe resulting mixture was stirred at room temperature overnight
  6. washwashed with water and 2M NaOH (2 ml each)
  7. customevaporated to dryness under reduced pressure
  8. customThe residue was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile)

Sources & evidence

ORD record
ord-1305db22f8584012a435e8e4486283d0
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Linked notes

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