Formic Acid → HCID 11849166, compound

HRID 2262751Notes

Reaction equation

HRID 2262751 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([N:12]2[C:16]3[CH:17]=[CH:18][C:19]([CH2:21][NH2:22])=[CH:20][C:15]=3[N:14]=[CH:13]2)[CH:9]=[CH:10][CH:11]=1.[CH:23](O)=[O:24]>>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([N:12]2[C:16]3[CH:17]=[CH:18][C:19]([CH2:21][NH:22][CH:23]=[O:24])=[CH:20][C:15]=3[N:14]=[CH:13]2)[CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 11983378HCID 11983378, compound

Product 1

HCID 11849166HCID 11849166, compoundYield 33%

Procedure

A solution of C-[1-(3-thiazol-2-yl-phenyl)-1H-benzoimidazol-5-yl]-methylamine (1.4 g, 4.57 mmol) in formic acid (20 ml) was stirred at reflux for 3 hours. The mixture was evaporated in vacuo and the residue was partitioned between ethyl acetate and saturated, aqueous sodium carbonate. The organic layer was dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of dichloromethane and methanol (9:1 v/v) as the eluent to afford the desired product 0.5 g (33%). LC-ESI-HRMS of [M+H]+ shows 335.095 Da. Calc. 335.096657 Da. dev. −4.9 ppm.

Workup

  1. temperatureat reflux for 3 hours
  2. customThe mixture was evaporated in vacuo
  3. customthe residue was partitioned between ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel using
  7. additiona mixture of dichloromethane and methanol (9:1 v/v) as the eluent

Sources & evidence

ORD record
ord-e50dc84337974971afb23418dd012aaa
Source dataset
uspto-grants-2010_12
Patent number
US07851490B2

Reaction notes

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