Hydrochloric Acid → HCID 66796666, compound

HRID 70215Notes

Reaction equation

HRID 70215 reaction equation
[ClH:1].O1CCOCC1.C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[S:22][CH:23]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[N:25]=2)[CH:17]([CH2:30][O:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[CH2:16]1)=O)(C)(C)C>CO>[ClH:1].[ClH:1].[N:34]1[CH:35]=[CH:36][CH:37]=[C:32]([O:31][CH2:30][CH:17]2[CH2:16][NH:15][CH2:20][CH2:19][N:18]2[C:21]2[S:22][CH:23]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[N:25]=2)[CH:33]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59671612Methyl 2-(4-(tert-butoxycarbonyl)-2-((pyridin-3-yloxy)methyl)piperazin-1-yl)thiazole-4-carboxylate

Product 1

HCID 66796666HCID 66796666, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4 M HCl in 1,4-dioxane (6 mL, 24 mmol) was added to a solution of methyl 2-(4-(tert-butoxycarbonyl)-2-((pyridin-3-yloxy)methyl)piperazin-1-yl)thiazole-4-carboxylate (32 mg, 0.074 mmol) in MeOH (1 mL). After stirring overnight, the reaction mixture was concentrated under reduced pressure. The material was dissolved in H2O (20 mL), and the pH was adjusted to ˜2 with concentrated HCl. This was washed with Et2O (3×5 mL, discarded). The aqueous layer was adjusted to pH ˜12 with 1 N NaOH and was extracted with EtOAc (3×20 mL). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure, yielding 5.0 mg (17%) of the title compound. LC-MS: RT=3.41 min, (M+H)+=335.4.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe material was dissolved in H2O (20 mL)
  3. washThis was washed with Et2O (3×5 mL, discarded)
  4. extractionwas extracted with EtOAc (3×20 mL)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-197079ca56d44a7cb148e9413a61801d
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

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