1-Methylimidazole → HCID 86658954, compound

HRID 516269Notes

Reaction equation

HRID 516269 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][C:7]3[CH2:15][CH2:14][N:13](C([O:18][C:19]([CH3:22])(C)C)=O)[CH2:12][CH2:11][C:8]=3[CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:30]([S:32](Cl)(=[O:34])=[O:33])[CH3:31].CN1C=CN=C1.CC[O:44][C:45]([CH3:47])=[O:46]>ClCCl.[Cl-].[Na+].O>[C:45]([OH:44])(=[O:46])/[CH:47]=[CH:22]/[C:19]([OH:18])=[O:33].[CH2:30]([S:32]([N:1]1[C:10]2[C:5](=[CH:6][C:7]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11][C:8]=3[CH:9]=2)[CH2:4][CH2:3][CH2:2]1)(=[O:34])=[O:33])[CH3:31]

Participants

8

Reactant 5

HCID 13901-MethylimidazoleHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11667Ethanesulfonyl chlorideHCID 66982459HCID 66982459, compound

Product 1

HCID 86658954HCID 86658954, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 200 mg of t-butyl 1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate in 6 ml of dichloromethane were added 0.148 ml of triethylamine, 0.093 ml of ethanesulfonyl chloride, and 54 mg of 1-methylimidazole under ice-cooling, followed by stirring at room temperature overnight. To the reaction mixture were added EtOAc and saturated brine, and the organic layer was washed with saturated brine and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc). The resulting substance was dissolved in 4 ml of chloroform, followed by adding 2 ml of trifluoroacetic acid and stirring for 30 minutes. After concentration under reduced pressure, the resultant was dissolved in 4.5 ml of EtOH, neutralized by the addition of triethylamine, and then concentrated under reduced pressure. Then, the residue was purified by silica gel column chromatography (elution solvent: chloroform-MeOH-aqueous ammonia). The resulting substance was dissolved in EtOH and 76 mg of fumaric acid was added thereto. The resulting white solid was collected by filtration and dried to obtain 61 mg of 1-(ethylsulfonyl)-2,3,4,6,7,8,9,10-octahydro-1H-azepino[4,5-g]quinoline monofumarate.

Workup

  1. temperaturecooling
  2. washthe organic layer was washed with saturated brine
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)
  5. dissolutionThe resulting substance was dissolved in 4 ml of chloroform
  6. additionby adding 2 ml of trifluoroacetic acid
  7. stirringstirring for 30 minutes
  8. concentrationAfter concentration under reduced pressure
  9. dissolutionthe resultant was dissolved in 4.5 ml of EtOH
  10. additionneutralized by the addition of triethylamine
  11. concentrationconcentrated under reduced pressure
  12. customThen, the residue was purified by silica gel column chromatography (elution solvent: chloroform-MeOH-aqueous ammonia)
  13. dissolutionThe resulting substance was dissolved in EtOH
  14. addition76 mg of fumaric acid was added
  15. filtrationThe resulting white solid was collected by filtration
  16. customdried

Sources & evidence

ORD record
ord-02d915890b67493582371794d3f26e59
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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