Hydrochloric Acid → 2-[(4-Methyl-2-thiazolyl)methoxy]-6-(1-piperazinyl)pyrazine

HRID 2182154Notes

Reaction equation

HRID 2182154 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[N:18][CH:17]=[C:16]([O:20][CH2:21][C:22]3[S:23][CH:24]=[C:25]([CH3:27])[N:26]=3)[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[CH3:27][C:25]1[N:26]=[C:22]([CH2:21][O:20][C:16]2[N:15]=[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH:19]=[N:18][CH:17]=2)[S:23][CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 697329301,1-Dimethylethyl 4-[6-[(ethylamino)carbonyl]-2-fluoro-3-pyridinyl]-1-piperazinecarboxylate

Product 1

HCID 224820202-[(4-Methyl-2-thiazolyl)methoxy]-6-(1-piperazinyl)pyrazineYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

6′-(4-Methyl-thiazol-2-ylmethoxy)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester (I-3u) (376 mg, 0.96 mmol) was dissolved in dry 1,4-dioxane (4 mL) and 4 M HCl in 1,4-dioxane (4 mL, 16 mmol) was added with stirring. A gummy solid immediately precipitated. Methanol (2 mL) was added to solubilize the solid. The resulting solution was stirred at room temperature for 4 h and concentrated to a gummy yellow solid. The residue was basified by addition of 1 M NaOH (15 mL) and extracted with CH2Cl2 (3×20 mL). The combine extracts were dried over Na2SO4 (anhydrous), filtered, and concentrated in vacuo to an amber oil. The oil solified on drying in vacuo to give the title compound 3-Q (274 mg, 98% yield).

Workup

  1. customA gummy solid immediately precipitated
  2. additionMethanol (2 mL) was added
  3. stirringThe resulting solution was stirred at room temperature for 4 h
  4. concentrationconcentrated to a gummy yellow solid
  5. additionThe residue was basified by addition of 1 M NaOH (15 mL)
  6. extractionextracted with CH2Cl2 (3×20 mL)
  7. dry with materialThe combine extracts were dried over Na2SO4 (anhydrous)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo to an amber oil
  10. customon drying in vacuo

Sources & evidence

ORD record
ord-763b2f03de664b5b9fe1982e93b1f45e
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

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