Hydrochloric Acid → n-(Benzo[d]thiazol-6-yl)-2-((pyridin-3-yloxy)methyl)piperazine-1-carboxamide

HRID 70155Notes

Reaction equation

HRID 70155 reaction equation
Cl.O1CCOCC1.OC(C(F)(F)F)=O.OC(C(F)(F)F)=O.[S:22]1[C:26]2[CH:27]=[C:28]([NH:31][C:32]([N:34]3[CH2:39][CH2:38][N:37](C(OC(C)(C)C)=O)[CH2:36][CH:35]3[CH2:47][O:48][C:49]3[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=3)=[O:33])[CH:29]=[CH:30][C:25]=2[N:24]=[CH:23]1>CO>[S:22]1[C:26]2[CH:27]=[C:28]([NH:31][C:32]([N:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH:35]3[CH2:47][O:48][C:49]3[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=3)=[O:33])[CH:29]=[CH:30][C:25]=2[N:24]=[CH:23]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131728850HCID 131728850, compound

Product 1

HCID 59671524n-(Benzo[d]thiazol-6-yl)-2-((pyridin-3-yloxy)methyl)piperazine-1-carboxamideYield 85.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4 M HCl in 1,4-dioxane (6 mL, 24 mmol) was added to a solution of tert-butyl 4-(benzo[d]thiazol-6-ylcarbamoyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate di-TFA salt (154 mg, 0.221 mmol) in MeOH (1 mL). After stirring overnight, the reaction mixture was concentrated under reduced pressure, dissolved in 1 N NaOH, and extracted with EtOAc (3×). The combined extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure, yielding 69.5 mg (85%) of the title compound as an off-white solid. LC-MS: RT=3.62 min, [M+H]+=370.1.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in 1 N NaOH
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4b1f7a728c924ed3b5a085862a391f3d
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

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