Acetic Acid → HCID 178491999, compound

HRID 1244320Notes

Reaction equation

HRID 1244320 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]([Cl: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>[Cl:26][C:23]1[N:22]=[C:21]2[NH:27][C:18]([C:16]3[S:17][C:5]4[C:6]([N:9]5[CH2:14][CH2:13][O:12][CH2:11][CH2:10]5)=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=4[N:15]=3)=[N:19][C:20]2=[CH:25][CH:24]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 679Dimethyl SulfoxideHCID 14923Ammonium HydroxideHCID 178492017HCID 178492017, compound

Product 1

HCID 178491999HCID 178491999, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1.0 g 5-Chloro-3H-imidazo[4,5-b]pyridine-2-carbothioic acid (2-methoxy-5-morpholin-4-yl-phenyl)-amide (2.5 mmol) was dissolved in ethyl acetate (7 ml), heated to reflux and treated with 0.87 ml HBr in AcOH (5.7M, 5.0 mmol) and 0.2 ml DMSO (3.0 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 0.91 g 5-chloro-2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3H-imidazo[4,5-b]pyridine (92%) as a yellow solid; M.p.: >300° C. (dec.).

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-a629c3db83e5413d8db1f8208afda737
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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