Benzylamine → HCID 68491961, compound

HRID 21034Notes

Reaction equation

HRID 21034 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH:20]=O)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29].[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][NH:37][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29]

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 866282274-Chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

Product 1

HCID 68491961HCID 68491961, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (20.0 mg, 0.0487 mmol) was dissolved in dichloromethane (0.5 mL), and the solution was added with benzylamine (0.011 mL, 0.10 mmol) and sodium triacetoxyborohydride (32 mg, 0.15 mmol) followed by stirring at room temperature for 16 hours. The reaction mixture was added with 3 mol/L aquous sodium hydroxide solution, extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate. The mixture was added with aldehyde resin and stirred at room temperature for 16 hours. The resin was filtered off and the solvent of the filtrate was evaporated under reduced pressure. The residue was dissolved in chloroform, and the solution was filtered through a column filled with SCX (positive-ion-exchange resin). The resulting SCX was washed with 7 mol/L ammonia-methanol solution and the solvent of the filtrate was evaporated under reduced pressure to obtain 4-chloro-7-[1-(tert-butoxycarbonyl)-5-(benzylaminomethyl)indol-2-yl]isoindolinone.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. additionThe mixture was added with aldehyde resin
  4. stirringstirred at room temperature for 16 hours
  5. filtrationThe resin was filtered off
  6. customthe solvent of the filtrate was evaporated under reduced pressure
  7. dissolutionThe residue was dissolved in chloroform
  8. filtrationthe solution was filtered through a column
  9. additionfilled with SCX (positive-ion-exchange resin)
  10. washThe resulting SCX was washed with 7 mol/L ammonia-methanol solution
  11. customthe solvent of the filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-17689cdcd57d4c7999384ea58e4cf18d
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

Loading…