Hydrochloric Acid → 2-(2-((Pyridin-3-yloxy)methyl)piperazin-1-yl)benzo[d]oxazole

HRID 70204Notes

Reaction equation

HRID 70204 reaction equation
Cl.O1CCOCC1.OC(C(F)(F)F)=O.OC(C(F)(F)F)=O.[O:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[C:23]1[N:31]1[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH:32]1[CH2:44][O:45][C:46]1[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=1>CO>[N:48]1[CH:49]=[CH:50][CH:51]=[C:46]([O:45][CH2:44][CH:32]2[CH2:33][NH:34][CH2:35][CH2:36][N:31]2[C:23]2[O:22][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[N:24]=2)[CH:47]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131728870HCID 131728870, compound

Product 1

HCID 596714972-(2-((Pyridin-3-yloxy)methyl)piperazin-1-yl)benzo[d]oxazole

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]oxazol-2-yl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate di-TFA salt (74 mg, 0.14 mmol) in MeOH (1 mL). After 1 h, the reaction mixture was concentrated under reduced pressure. The material was dissolved in EtOAc (40 mL), washed with 1 N NaOH (2×20 mL) and brine (20 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. This gave 34.7 mg (79%) of the desired product as a thick yellow oil. LC-MS: RT=4.00 min, [M+H]+=311.1.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe material was dissolved in EtOAc (40 mL)
  3. washwashed with 1 N NaOH (2×20 mL) and brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5cb131a0c7544ff6a1dd83e1204f9d81
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

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