2-(Ethylamino)ethanol → N-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butoxy}-phenyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide

HRID 1841598Notes

Reaction equation

HRID 1841598 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:27])[S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])=[CH:9][CH:8]=1.[CH2:28]([NH:30][CH2:31][CH2:32][OH:33])[CH3:29]>CC(N(C)C)=O>[CH2:28]([N:30]([CH2:31][CH2:32][OH:33])[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:27])[S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])=[CH:9][CH:8]=1)[CH3:29]

Participants

4

Reactant 2

HCID 80722-(Ethylamino)ethanol2×HCID 23446540N-[4-(4-Bromo-butoxy)-phenyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide

Product 1

HCID 10183939N-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butoxy}-phenyl)-N-methyl-4-trifluoromethyl-benzenesulfonamideYield 76%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 466 mg (1 mmol) of N-[4-(4-Bromo-butoxy)-phenyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide 69-9844 in 3.5 ml DMA was treated at 0° C. with 0.195 ml (2 mmol) of 2-ethylaminoethanol and stirred at RT for 15 h. The reaction mixture was cooled (0° C.) again, treated with 0.195 ml (2 mmol) of 2-ethylaminoethanol and stirred at RT for further 24 h. The solution was concentrated, the residual oil was dissolved in water/acetontrile 1:1/5% formic acid and purified by prep. HPLC: RP-18, acetonitrile/water, 10%-60% acetonitrile. The pure fractions were collected, dissolved in EtOAc, washed with aqueous sat. NaHCO3 solution, and the organic phase was dried (Na2SO4) and evaporated to yield 360 mg (76%) of N-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butoxy}-phenyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide, MS: 475 (MH+).

Workup

  1. temperatureThe reaction mixture was cooled (0° C.) again
  2. stirringstirred at RT for further 24 h
  3. concentrationThe solution was concentrated
  4. dissolutionthe residual oil was dissolved in water/
  5. custom1/5% formic acid and purified by prep
  6. customThe pure fractions were collected
  7. dissolutiondissolved in EtOAc
  8. washwashed with aqueous sat. NaHCO3 solution
  9. dry with materialthe organic phase was dried (Na2SO4)
  10. customevaporated

Sources & evidence

ORD record
ord-44cb6206f3824baebb14b747c33bbfb0
Source dataset
uspto-grants-2004_01
Patent number
US06683201B2

Reaction notes

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