Triethylamine → (E)-3-methyl-N-[2-[(2-methyl-4-quinolyl)amino]ethyl]but-1-ene-1-sulfonamide

HRID 333080Notes

Reaction equation

HRID 333080 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([NH:12][CH2:13][CH2:14][NH2:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[CH3:23][CH:24]([CH3:31])/[CH:25]=[CH:26]/[S:27](Cl)(=[O:29])=[O:28]>C(#N)C.ClCCl>[CH3:23][CH:24]([CH3:31])/[CH:25]=[CH:26]/[S:27]([NH:15][CH2:14][CH2:13][NH:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([CH3:1])[CH:11]=1)(=[O:29])=[O:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6471895N1-(2-Methylquinolin-4-yl)ethane-1,2-diamineHCID 86691168(E)-3-Methylbut-1-ene-1-sulfonyl chloride

Product 1

HCID 56947602(E)-3-methyl-N-[2-[(2-methyl-4-quinolyl)amino]ethyl]but-1-ene-1-sulfonamideYield 41.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N1-(2-methylquinolin-4-yl)ethane-1,2-diamine (161 mg, 0.800 mmol) and triethylamine (0.350 ml, 2.51 mmol) in acetonitrile (5 ml) was added a solution of (E)-3-methylbut-1-ene-1-sulfonyl chloride (102 mg of step D) in dichloromethane (1 ml). The mixture was stirred 30 minutes at room temperature, concentrated under reduced pressure and the residue was purified by column chromatography over aluminum oxide using a gradient of methanol (2-10%) in dichloromethane to yield 83 mg of an off-white foam (0.25 mmol; 13% over 4 steps).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue was purified by column chromatography over aluminum oxide using a gradient of methanol (2-10%) in dichloromethane

Sources & evidence

ORD record
ord-49334b400c5c4528af3ad05d34d0f595
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

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