N-bromobutanimide → HCID 86711607, compound

HRID 527338Notes

Reaction equation

HRID 527338 reaction equation
[C:1]([N:3]=[S:4]([C:7]1[CH:30]=[CH:29][C:10]([CH2:11][NH:12][C:13]([C:15]2[C:20](=[O:21])[CH:19]=[C:18]([CH3:22])[N:17]([C:23]3[N:24]([CH3:28])[N:25]=[CH:26][CH:27]=3)[CH:16]=2)=[O:14])=[CH:9][CH:8]=1)([CH3:6])=[O:5])#[N:2].[Br:31]N1C(=O)CCC1=O>ClCCl.C(O)(=O)C>[C:1]([N:3]=[S:4]([C:7]1[CH:8]=[CH:9][C:10]([CH2:11][NH:12][C:13]([C:15]2[C:20](=[O:21])[C:19]([Br:31])=[C:18]([CH3:22])[N:17]([C:23]3[N:24]([CH3:28])[N:25]=[CH:26][CH:27]=3)[CH:16]=2)=[O:14])=[CH:29][CH:30]=1)([CH3:6])=[O:5])#[N:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 86711608HCID 86711608, compound

Product 1

HCID 86711607HCID 86711607, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-methyl-1-(2-methyl-2H-pyrazol-3-yl)-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-(N-cyano-S-methylsulfonimidoyl)-benzylamide (preparation 4b, 150 mg, 0.118 mmol) in dichloromethane (2 mL) is added N-bromosuccinimide (21 mg, 0.35 mmol) and five drops of glacial acetic acid. After stirring for 18 h at room temperature the reaction mixture is concentrated under reduced pressure and purified by preparative reversed phase HPLC (Xbridge, gradient of acetonitrile in water, 0.1% TFA, 60° C.). Yield: 40 mg (23% of theory); ESI mass spectrum: [M+H]+=503 (bromine isotope pattern); r.t. HPLC: 0.82 min (Z012_S04).

Workup

  1. concentrationis concentrated under reduced pressure
  2. custompurified by preparative reversed phase HPLC (Xbridge, gradient of acetonitrile in water, 0.1% TFA, 60° C.)
  3. customr.t
  4. custom0.82 min (Z012_S04)

Sources & evidence

ORD record
ord-d637bd1fd8b44ccd87768fa16d0e3d30
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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