Chlorosuccinimide → HCID 178501960, compound

HRID 1053834Notes

Reaction equation

HRID 1053834 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:16][C:15]([C@@H:17]3[CH2:21][C@H:20]([CH:22]4[CH2:27][CH2:26][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][CH2:23]4)[CH2:19][N:18]3[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[N:14][CH:13]=2)=[CH:8][CH:7]=1)=[O:4].[Cl:39]N1C(=O)CCC1=O>C(#N)C.CN(C)C=O>[Cl:39][C:13]1[N:14]=[C:15]([C@@H:17]2[CH2:21][C@H:20]([CH:22]3[CH2:23][CH2:24][N:25]([S:28]([CH3:31])(=[O:29])=[O:30])[CH2:26][CH2:27]3)[CH2:19][N:18]2[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[NH:16][C:12]=1[C:9]1[CH:8]=[CH:7][C:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 1317363052-methyl-2-propanyl (2S,4R)-2-(5-{4-[(methoxycarbonyl)amino]phenyl}-1H-imidazol-2-yl)-4-[1-(methylsulfonyl)-4-piperidinyl]-1-pyrrolidinecarboxylate

Product 1

HCID 178501960HCID 178501960, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of the compound prepared in Example 64 (2.41 g, 4.4 mmol) in acetonitrile (50 mL) and N,N-dimethylformamide (20 mL) at 0° C. was added N-chlorosuccinimide (0.62 g, 4.6 mmol). The reaction was warmed to room temperature, stirred under nitrogen overnight then heated between 50-70° C. for 2 h. The reaction was cooled to room temperature, concentrated under reduced pressure and the residue washed with aqueous sodium bicarbonate solution (1×50 mL). The solid residue was suspended in a mixture of ethyl acetate (100 mL) and dichloromethane (100 mL) and sonicated. The solids were collected by filtration to give the title compound (1.39 g) as an off-white solid.

Workup

  1. temperaturethen heated between 50-70° C. for 2 h
  2. temperatureThe reaction was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. washthe residue washed with aqueous sodium bicarbonate solution (1×50 mL)
  5. additionThe solid residue was suspended in a mixture of ethyl acetate (100 mL) and dichloromethane (100 mL)
  6. customsonicated
  7. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-3c5329a62a844b8ea72dcf4c54cc67f6
Source dataset
uspto-grants-2016_07
Patent number
US09394250B2

Reaction notes

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