Chloroacetone → HCID 67055861, compound

HRID 2036800Notes

Reaction equation

HRID 2036800 reaction equation
[NH2:1][C:2]1[C:7]([S:8]([NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])=[O:9])=[CH:6][C:5]([Br:16])=[CH:4][N:3]=1.Cl[CH2:18][C:19](=O)[CH3:20]>C(O)C>[Br:16][C:5]1[CH:6]=[C:7]([S:8]([NH:11][C:12]([CH3:13])([CH3:15])[CH3:14])(=[O:10])=[O:9])[C:2]2[N:3]([CH:18]=[C:19]([CH3:20])[N:1]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 62148617HCID 62148617, compound

Product 1

HCID 67055861HCID 67055861, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-amino-5-bromo-N-tert-butylpyridine-3-sulfonamide (3.0 g, 9.7 mmol) in ethanol (6 mL) was added chloroacetone (3.0 mL, 48 mmol) and the reaction mixture was stirred at 80° C. for 48 h. The solvents were evaporated under reduced pressure and the residue was purified by flash silica gel column chromatography (5% methanol in DCM) to yield 6-bromo-N-tert-butyl-2-methylimidazo[1,2-a]pyridine-8-sulfonamide (2.2 g, 66%), which was used without further purification. LCMS Method T: retention time 1.33 min; [M+1]=346.64.

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. customthe residue was purified by flash silica gel column chromatography (5% methanol in DCM)

Sources & evidence

ORD record
ord-7a387e572f88485ca3fb25a2df2736da
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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