Diisopropylethylamine → HCID 17940104, compound

HRID 429146Notes

Reaction equation

HRID 429146 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]([F:25])([F:24])[F:23])[CH:20]=3)[CH2:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][C:4]=1[N:26]1[CH2:31][CH2:30][N:29](C)[CH2:28][CH2:27]1.[Cl:33]C(OC(Cl)C)=O.C(N(CC)C(C)C)(C)C>ClCCCl>[ClH:33].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]([F:25])([F:23])[F:24])[CH:20]=3)[CH2:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][C:4]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 18354571HCID 18354571, compound

Product 1

HCID 17940104HCID 17940104, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 1-[4-methoxy-3-(4-methylpiperazin-1-yl)benzenesulfonyl]-7-trifluoromethyl-1,2,3,4-tetrahydroquinoline (E8) (70 mg, 0.15 mmol) and 1-chloro-ethyl chloroformate (0.08 ml, 0.75 mmol) in 1,2-dichloroethane (2 ml) was heated under reflux for 18 h, and then was cooled to ambient temperature. N,N-Diisopropylethylamine (0.05 ml, 0.26 mmol) was added and the resulting solution was heated under reflux for 2 h. The solvent was removed, the residue was dissolved in methanol (4 ml), and the reaction was heated under reflux for 18 h. The solvent was partially removed, dichloromethane (20 ml) was added, and the solution was washed with saturated aqueous sodium hydrogen carbonate (10 ml), dried (MgSO4), and then evaporated. The residue was purified by column chromatography on silica gel eluting with a methanol-dichloromethane gradient to afford the sulfonamide derivative as a yellowish oil. The oil was dissolved in acetone (0.5 ml) and 1M solution of hydrogen chloride in diethyl ether (0.1 ml) was added. The solution was evaporated, and the residue was coevaporated with dry benzene (3×2 ml) to give the title compound (E25) as a cream solid (38 mg, 52%).

Workup

  1. temperatureunder reflux for 18 h
  2. temperaturethe resulting solution was heated
  3. temperatureunder reflux for 2 h
  4. customThe solvent was removed
  5. dissolutionthe residue was dissolved in methanol (4 ml)
  6. temperaturethe reaction was heated
  7. temperatureunder reflux for 18 h
  8. customThe solvent was partially removed
  9. additiondichloromethane (20 ml) was added
  10. washthe solution was washed with saturated aqueous sodium hydrogen carbonate (10 ml)
  11. dry with materialdried (MgSO4)
  12. customevaporated
  13. customThe residue was purified by column chromatography on silica gel eluting with a methanol-dichloromethane gradient

Sources & evidence

ORD record
ord-dc182ff8b0434536a0d2242622f6f3de
Source dataset
uspto-grants-2001_11
Patent number
US06316450B1

Reaction notes

Loading…