1,4-Dioxane hydrochloride → HCID 178503322, compound

HRID 1798901Notes

Reaction equation

HRID 1798901 reaction equation
Cl.O1CCOCC1.[CH3:8][S:9][C:10]1[N:11]=[C:12]2[C:21]3[C:16](=[N:17][NH:18][C:19]=3[N:20]=1)[CH:15](C(O)=O)[CH2:14][N:13]2[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCOCC1>[CH3:8][S:9][C:10]1[N:11]=[C:12]2[C:21]3[C:16](=[N:17][NH:18][C:19]=3[N:20]=1)[CH2:15][CH2:14][N:13]2[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 178503325HCID 178503325, compound

Product 1

HCID 178503322HCID 178503322, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4 M dioxane-HCl (300 mL) was added to crude 7-(methylthio)-5-phenyl-1,3,4,5-tetrahydro-1,2,5,6,8-pentaazaacenaphthylene-3-carboxylic acid (20 g) and the mixture was refluxed for 16 h. Upon completion of reaction after 16 h (monitored by LCMS), dioxane was removed under reduced pressure and saturated NaHCO3 solution (200 mL) was added. The reaction mixture was then extracted with dichloromethane (150 mL×3). The combined organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by silica gel column chromatography (using 0-10% tetrahydrofuran in dichloromethane) to provide 7-(methylthio)-5-phenyl-1,3,4,5-tetrahydro-1,2,5,6,8-pentaazaacenaphthylene as a white solid after recrystalized from ethyl acetate (4.2 g, 26.7% yield for three steps). 1H NMR (DMSO-d6, 400 MHz) δ 13.02 (s, 1H); 7.53-7.23 (m, 5H); 4.19 (t, J=6.4 Hz, 2H); 3.21 (t, J=6.4 Hz, 2H); 2.42 (s, 3H). LCMS [M+H]: 284 HPLC: 98.28% (254 nm)

Workup

  1. temperaturethe mixture was refluxed for 16 h
  2. customwas removed under reduced pressure and saturated NaHCO3 solution (200 mL)
  3. additionwas added
  4. extractionThe reaction mixture was then extracted with dichloromethane (150 mL×3)
  5. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue
  9. customThe residue was purified by silica gel column chromatography (using 0-10% tetrahydrofuran in dichloromethane)

Sources & evidence

ORD record
ord-e0fec1682bde49c2a4437835df980f85
Source dataset
uspto-grants-2013_01
Patent number
US08343983B2

Reaction notes

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