Acetic Acid → HCID 178492000, compound

HRID 1244318Notes

Reaction equation

HRID 1244318 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][C:4]=1[NH:15][C:16]([C:18]1[NH:27][C:21]2=[N:22][C:23]([CH3:26])=[CH:24][CH:25]=[C:20]2[N:19]=1)=[S:17].Br.CC(O)=O.CS(C)=O.[OH-].[NH4+]>C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[C:4]2[N:15]=[C:16]([C:18]3[NH:27][C:21]4=[N:22][C:23]([CH3:26])=[CH:24][CH:25]=[C:20]4[N:19]=3)[S:17][C:5]=2[C:6]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)=[CH:7][CH:8]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 679Dimethyl SulfoxideHCID 14923Ammonium HydroxideHCID 178492018HCID 178492018, compound

Product 1

HCID 178492000HCID 178492000, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

0.3 g 5-Methyl-3H-imidazo[4,5-b]pyridine-2-carbothioic acid (2-methoxy-5-morpholin-4-yl-phenyl)-amide (0.8 mmol) was dissolved in ethyl acetate (3 ml), heated to reflux and treated with 0.27 ml HBr in AcOH (5.7M, 1.6 mmol) and 0.067 ml DMSO (0.94 mmol). Stirring at reflux was continued for 2 h. Upon cooling a precipitation formed, which was isolated and dissolved in water (2 ml). The pH was adjusted to 10 with 25% ammonium hydroxide in water. Once again a precipitation formed, which was filtered. The residue on the filter was washed with water and dried in vacuo. One obtained 0.125 g 2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-5-methyl-3H-imidazo[4,5-b]pyridine (42%) as a yellow solid; M.p.: 200–210° C.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperatureat reflux
  4. temperatureUpon cooling
  5. customa precipitation
  6. customformed
  7. customwhich was isolated
  8. customOnce again a precipitation
  9. customformed
  10. filtrationwhich was filtered
  11. washThe residue on the filter was washed with water
  12. customdried in vacuo

Sources & evidence

ORD record
ord-ae3b39c27c874c67b567bbd06fafeeb3
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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