tert-Butyl hydroperoxide → HCID 25235265, compound

HRID 1043654Notes

Reaction equation

HRID 1043654 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[S:7][C:6]2=[N:8][CH:9]=[C:10]([CH:11]=[O:12])[N:5]2[N:4]=1.[CH3:14][NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(OO)(C)(C)C>C(#N)C.O>[CH2:16]([N:15]([CH3:14])[C:11]([C:10]1[N:5]2[C:6]([S:7][C:3]([N:2]([CH3:13])[CH3:1])=[N:4]2)=[N:8][CH:9]=1)=[O:12])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 7669N-MethylbenzylamineHCID 86762101HCID 86762101, compound

Product 1

HCID 25235265HCID 25235265, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

2-Dimethylamino-imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde (116 mg, 0.591 mmol) was dissolved in dry acetonitrile (4 mL) and N-methylbenzylamine (0.768 mmol, 0.1 mL) and t-butylhydroperoxide (0.768 mmol, 5.5M, 0.14 mL) were added. The mixture was heated at 80° C. for 10 hours. The reaction mixture was diluted with water (4 mL) at room temperature and extracted with dichloromethane (3×8 mL). The combined organic layer was dried over sodium sulphate and concentrated in vacuo. The crude product was purified by flash chromatography (Isolute cartridge SiII, ethyl acetate:dichloromethane, 1:9 to 10:0) yielding 54 mg of 2-dimethylamino-imidazo[2,1-b][1,3,4]thiadiazole-5-carboxylic acid benzyl-methyl-amide as yellowish solid (29% yield).

Workup

  1. extractionextracted with dichloromethane (3×8 mL)
  2. dry with materialThe combined organic layer was dried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography (Isolute cartridge SiII, ethyl acetate:dichloromethane, 1:9 to 10:0)

Sources & evidence

ORD record
ord-ba675581e3fc416bab695ae3e54e89f4
Source dataset
uspto-grants-2013_10
Patent number
US08563550B2

Reaction notes

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