Triethylamine → 2-[(2-Methoxy-4-quinolyl-amino]ethyl]hex-2-enamide

HRID 333056Notes

Reaction equation

HRID 333056 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([NH:13][CH2:14][CH2:15]N)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.C([N:19](CC)CC)C.[C:24](Cl)(=[O:30])/[CH:25]=[CH:26]/[CH2:27][CH2:28][CH3:29]>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([NH:13][CH2:14][CH2:15][C:25](=[CH:26][CH2:27][CH2:28][CH3:29])[C:24]([NH2:19])=[O:30])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5706484(E)-hex-2-enoyl chlorideHCID 66835195HCID 66835195, compound

Product 1

HCID 866911612-[(2-Methoxy-4-quinolyl-amino]ethyl]hex-2-enamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(2-Methoxy-4-quinolyl)ethane-1,2-diamine (21.7 mg, 0.1 mmol) was dissolved in anhydrous dichloromethane (1 ml) together with triethylamine (17.4 μl, 0.125 mmol). (E)-hex-2-enoyl chloride (16.6 mg, 0.125 mmol) was added and the mixture was shaken for 10 minutes, diluted with dichloromethane and washed with 10% sodium bicarbonate solution (2 times), water and evaporated to dryness under reduced pressure. The resulting residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 3.4 mg (0.0109 mmol, 11%).

Workup

  1. washwashed with 10% sodium bicarbonate solution (2 times), water
  2. customevaporated to dryness under reduced pressure
  3. customThe resulting residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
  4. customto yield 3.4 mg (0.0109 mmol, 11%)

Sources & evidence

ORD record
ord-2654af2edd8a4d9b844906dc790a4e64
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

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