Hydrogen Sulfide → HCID 69697293, compound

HRID 412591Notes

Reaction equation

HRID 412591 reaction equation
S.[CH2:2]([O:4][C:5]([C:7]1([CH2:19][O:20][C:21]2[C:30]([Cl:31])=[C:29]3[C:24]([CH:25]=[CH:26][C:27]([C:32]#[N:33])=[CH:28]3)=[CH:23][CH:22]=2)[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:3].[N:34]1C=CC=CC=1>C(N(CC)CC)C>[ClH:31].[ClH:31].[CH2:2]([O:4][C:5]([C:7]1([CH2:19][O:20][C:21]2[C:30]([Cl:31])=[C:29]3[C:24]([CH:25]=[CH:26][C:27]([C:32](=[NH:34])[NH2:33])=[CH:28]3)=[CH:23][CH:22]=2)[CH2:8][CH2:9][N:10]([C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)[CH2:11][CH2:12]1)=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 1049PyridineHCID 69697631HCID 69697631, compound

Product 1

HCID 69697293HCID 69697293, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Hydrogen sulfide was blown into a solution of 4-(8-chloro-2-cyanonaphthalen-7-yloxymethyl)-1-(pyridin-4-yl)piperidine-4-carboxylic acid ethyl ester (124 mg) in a mixture of pyridine (2.5 ml) and triethylamine (0.5 ml) with ice-cooling, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solvent was evaporated and the residue was treated with hydrogen chloride-ethanol. To the residue were added acetone (2 ml), methanol (2 ml) and methyl iodide (0.172 ml), and the mixture was stirred under reflux for 2 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was dissolved in ethanol (4 ml). Ammonium acetate (106 mg) was added, and the mixture was stirred at 75° C. for 2 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was purified by silica gel column chromatography (chloroform:methanol:ammonia). The obtained residue was treated with hydrogen chloride-ethanol and dried under reduced pressure to give the title compound (92 mg).

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated
  4. additionthe residue was treated with hydrogen chloride-ethanol
  5. additionTo the residue were added acetone (2 ml), methanol (2 ml) and methyl iodide (0.172 ml)
  6. stirringthe mixture was stirred
  7. temperatureunder reflux for 2 hours
  8. customAfter completion of the reaction
  9. customthe solvent was evaporated
  10. dissolutionthe obtained residue was dissolved in ethanol (4 ml)
  11. additionAmmonium acetate (106 mg) was added
  12. stirringthe mixture was stirred at 75° C. for 2 hours
  13. customAfter completion of the reaction
  14. customthe solvent was evaporated
  15. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol:ammonia)
  16. additionThe obtained residue was treated with hydrogen chloride-ethanol
  17. customdried under reduced pressure

Sources & evidence

ORD record
ord-ad8191a7d33440bdb809d34a974dafca
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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