HCID 57471433, compound → HCID 57467342, compound

HRID 510549Notes

Reaction equation

HRID 510549 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1Cl)[CH2:5][CH:6]1[C:15]2[CH:14]=[C:13]([CH2:16][CH2:17][CH2:18][NH:19][S:20]([CH2:23][CH2:24][CH3:25])(=[O:22])=[O:21])[CH:12]=[CH:11][C:10]=2[CH2:9][CH2:8][CH:7]1[NH:26][CH:27]([CH3:29])[CH3:28].[H][H]>CO.[OH-].[Pd+2].[OH-]>[ClH:1].[CH2:5]([CH:6]1[C:15]2[CH:14]=[C:13]([CH2:16][CH2:17][CH2:18][NH:19][S:20]([CH2:23][CH2:24][CH3:25])(=[O:21])=[O:22])[CH:12]=[CH:11][C:10]=2[CH2:9][CH2:8][CH:7]1[NH:26][CH:27]([CH3:28])[CH3:29])[C:4]1[CH:30]=[CH:31][CH:32]=[CH:2][CH:3]=1

Participants

5

Reactant 2

HCID 57471433HCID 57471433, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57467342HCID 57467342, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

N-{3-[8-(3,4-Dichlorobenzyl)-7-(propan-2-ylamino)-5,6,7,8-tetrahydronaphthalen-2-yl]propyl}propane-1-sulfonamide (70 mg, 0.137 mmol) was dissolved in methanol (1.5 mL) and palladium hydroxide (30 mg, 0.214 mmol) was added. The reaction mixture was heated under reflux in an atmosphere of hydrogen for 6 h. The catalyst was removed by filtration and the crude product was purified by flash chromatography (silica gel, dichloromethane, methanol). The obtained amine was dissolved in dichloromethane (2 mL) and 5 N hydrochloric acid in isopropanol (0.3 mL) was added. The solvent was evaporated and the product dried in vacuo. Yield: 30 mg (0.63 mmol, 46%).

Workup

  1. temperatureThe reaction mixture was heated
  2. customThe catalyst was removed by filtration
  3. customthe crude product was purified by flash chromatography (silica gel, dichloromethane, methanol)
  4. dissolutionThe obtained amine was dissolved in dichloromethane (2 mL)
  5. addition5 N hydrochloric acid in isopropanol (0.3 mL) was added
  6. customThe solvent was evaporated
  7. customthe product dried in vacuo

Sources & evidence

ORD record
ord-37b303b7e6e848bdb80c217637058344
Source dataset
uspto-grants-2015_08
Patent number
US09096619B2

Reaction notes

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