HCID 59608077, compound → HCID 25057271, compound

HRID 1690048Notes

Reaction equation

HRID 1690048 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]1[N:14]2[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]2=[N:12][C:11]=1[C:20]1[CH:33]=[CH:32][CH:31]=[CH:30][C:21]=1[C:22]([NH:24][NH:25][C:26]([NH:28][CH3:29])=S)=[O:23]>CO.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]1[N:14]2[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]2=[N:12][C:11]=1[C:20]1[CH:33]=[CH:32][CH:31]=[CH:30][C:21]=1[C:22]1[O:23][C:26]([NH:28][CH3:29])=[N:25][N:24]=1

Participants

4

Reactant 1

HCID 59608077HCID 59608077, compound

Product 1

HCID 25057271HCID 25057271, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 887MethanolSolvent

Procedure

3.2 117 mg (0.253 mmol) of 1-{2-[3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridin-2-yl]benzoyl}-4-methyl-3-thiosemicarbazide and 96 mg (0.300 mmol) of mercury(II) acetate are warmed at 80° C. for 1 hour in 10 ml of methanol in a sealed screw-lid bottle. The mixture is filtered through kieselguhr, rinsed with MeOH, and the filtrate is evaporated to dryness. Purification by silica-gel chromatography (heptane/ethyl acetate) gives 28 mg of (2,6-dimethylphenyl)-{6-fluoro-2-[2-(5-methylamino-1,3,4-oxadiazol-2-yl)phenyl]imidazo[1,2-a]pyridin-3-yl}amine, corresponding to a yield of 26%; MS-FAB (M+H+)=429.8; Rf (HPLC, polar method): 1.58 min.

Workup

  1. filtrationThe mixture is filtered through kieselguhr
  2. washrinsed with MeOH
  3. customthe filtrate is evaporated to dryness
  4. customPurification by silica-gel chromatography (heptane/ethyl acetate)

Sources & evidence

ORD record
ord-89edc3487a164bac84589e2e5a9a6c99
Source dataset
uspto-grants-2012_04
Patent number
US08153649B2

Reaction notes

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