N-bromobutanimide → HCID 135961994, compound

HRID 2233595Notes

Reaction equation

HRID 2233595 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][C:11]2[S:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)=[N:13][C:12]=2[CH3:26])[CH:6]=[CH:5][C:4]=1[C:27]1[NH:31][C:30](=[O:32])[O:29][N:28]=1.[Br:33]N1C(=O)CCC1=O>C(#N)C>[Br:33][C:6]1[C:7]([O:9][CH2:10][C:11]2[S:15][C:14]([C:16]3[CH:17]=[CH:18][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:20][CH:21]=3)=[N:13][C:12]=2[CH3:26])=[CH:8][C:3]([O:2][CH3:1])=[C:4]([C:27]2[NH:31][C:30](=[O:32])[O:29][N:28]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 135870790HCID 135870790, compound

Product 1

HCID 135961994HCID 135961994, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 100 mg of 3-{2-methoxy-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-[1,2,4]oxadiazol-5-one in 1 ml of acetonitrile was added 0.08 g of N-bromosuccinimide. The resulting mixture was heated to 70° C. overnight, concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (gradient of dichloromethane/methanol from 100/0 to 94/6) and washed with 94/6 dichloromethane/methanol to give 35 mg of 3-{5-bromo-2-methoxy-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-[1,2,4]oxadiazol-5-one.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was purified by column chromatography on silica gel (gradient of dichloromethane/methanol from 100/0 to 94/6)
  3. washwashed with 94/6 dichloromethane/methanol

Sources & evidence

ORD record
ord-cd2fad6bb4064657a94423033cdbcdf2
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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