Water → HCID 68491707, compound

HRID 21228Notes

Reaction equation

HRID 21228 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:34].N1C=CC=CC=1.[CH3:41][S:42](Cl)(=[O:44])=[O:43].O>ClCCl>[CH3:41][S:42]([NH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:34])(=[O:44])=[O:43]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 68492726HCID 68492726, compound

Product 1

HCID 68491707HCID 68491707, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Amino-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0820 g, 0.178 mmol) was dissolved in dichloromethane (4.0 mL), and the solution was added with pyridine (0.0430 mL, 0.534 mmol) and methanesulfonyl chloride (0.0210 mL, 0.267 mmol), followed by stirring for 1.5 hours under ice-cooling. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography (chloroform/methanol=4/1) to obtain 4-methanesulfonylamino-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0423 g, yield 44%).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by flash column chromatography (chloroform/methanol=4/1)

Sources & evidence

ORD record
ord-834ac04232764a4a848c5a8e74c30b86
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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