Potassium Carbonate → HCID 67236548, compound

HRID 447158Notes

Reaction equation

HRID 447158 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.C([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)(OC(C)(C)C)=O.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)C(O)=O.ClCCl>C(#N)C>[N:22]1([C:2]2[S:3][C:4]3[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:7][C:5]=3[N:6]=2)[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 21863450Trifluoroacetic acid methylene chlorideHCID 46911877Methyl 2-bromobenzo[d]thiazole-6-carboxylate

Product 1

HCID 67236548HCID 67236548, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 2-bromobenzo[d]thiazole-6-carboxylate (0.52 g, 1.90 mmol), Boc-piperazine (0.44 g. 2.38 mmol) and potassium carbonate (0.53 g, 3.80 mmol) were suspended in acetonitrile (21 ml) and refluxed overnight. The resulting mixture was then cooled to room temperature, concentrated in vacuo to approximately 2 ml, diluted with water and extracted with ethyl acetate. The organic layer was dried (MgSO4) and concentrated in vacuo to yield a residue which was treated with trifluoroacetic acid/dichloromethane (6 ml, 1:1) for 1.5 hrs. The resulting mixture was concentrated in vacuo, the resulting residue was dissolved in dichloromethane and washed with saturated sodium bicarbonate to yield methyl 2-(piperazin-1-yl)benzo[d]thiazole-6-carboxylate.

Workup

  1. temperaturerefluxed overnight
  2. concentrationconcentrated in vacuo to approximately 2 ml
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto yield a residue which
  8. concentrationThe resulting mixture was concentrated in vacuo
  9. dissolutionthe resulting residue was dissolved in dichloromethane
  10. washwashed with saturated sodium bicarbonate

Sources & evidence

ORD record
ord-67529be9aa914bdfa4b8f415c0ecf444
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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