N-bromobutanimide → HCID 67227234, compound

HRID 1043165Notes

Reaction equation

HRID 1043165 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([O:10][C:11]3[CH:20]=[C:19]([N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)[CH:18]=[CH:17][C:12]=3[C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Br:27]N1C(=O)CCC1=O>ClCCl.CN(C)C=O>[Br:27][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][C:5]=2[O:10][C:11]2[CH:20]=[C:19]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[CH:18]=[CH:17][C:12]=2[C:13]([O:15][CH3:16])=[O:14])[NH:1][CH:2]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 67227144HCID 67227144, compound

Product 1

HCID 67227234HCID 67227234, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of EXAMPLE 339B (1 g) in dichloromethane (50 mL) and N,N-dimethylformamide (5 mL) was cooled in an ice bath. N-bromosuccinimide (0.582 g) was added and the mixture was stirred overnight while warming to ambient temperature. The reaction was concentrated and the crude product was chromatographed on silica gel with a methanol/methylene chloride gradient.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe crude product was chromatographed on silica gel with a methanol/methylene chloride gradient

Sources & evidence

ORD record
ord-1c558ae0c7084c6c8364e373c7394fea
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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