1,4-Dioxane → HCID 22053597, compound

HRID 1829649Notes

Reaction equation

HRID 1829649 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.O1CCOCC1.[F:25][C:26]([F:62])([F:61])[C:27]1[CH:28]=[C:29]([CH:54]=[C:55]([C:57]([F:60])([F:59])[F:58])[CH:56]=1)[CH2:30][N:31]1[CH2:38][CH2:37][CH2:36][NH:35][C:34]2[N:39]=[C:40](S(C)(=O)=O)[N:41]=[C:42]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:33]=2[C:32]1=[O:53]>C(OCC)(=O)C>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:40]2[N:41]=[C:42]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:33]3[C:32](=[O:53])[N:31]([CH2:30][C:29]4[CH:54]=[C:55]([C:57]([F:60])([F:59])[F:58])[CH:56]=[C:27]([C:26]([F:62])([F:25])[F:61])[CH:28]=4)[CH2:38][CH2:37][CH2:36][NH:35][C:34]=3[N:39]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 837951-AcetylpiperazineHCID 22053574HCID 22053574, compound

Product 1

HCID 22053597HCID 22053597, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-acetylpiperazine(23.1 mg), diisopropylethylamine(0.1 mL), and 1,4-dioxane (1 mL) were added to 6-[3,5-bis(trifluoromethyl)benzyl]-5,6,7,8,9,10-hexahydro-2-(methylsulfonyl)-5-oxo-4-phenylpyrimido[4,5-b][1,5]diazocine (Compound of Reference Example 16; 83.8 mg). While heated, the mixture was refluxed for 5 hours. Subsequently, the reaction mixture was diluted with ethyl acetate, was sequentially washed with water and a saturated aqueous solution of sodium chloride, and was then dried over anhydrous sodium sulfate. Following removal of the solvent, the residue was purified on a silica gel column chromatography (ethyl acetate:methanol=10:1) to obtain 2-(4-acetylpiperazine-1-yl)-6-[3,5-bis(trifluoromethyl)benzyl]-5,6,7,8,9,10-hexahydro-5-oxo-4-phenylpyrimido[4,5-b][1,5]diazocine (63.0 mg, 69%).

Workup

  1. temperatureWhile heated
  2. temperaturethe mixture was refluxed for 5 hours
  3. washwas sequentially washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, and was then dried over anhydrous sodium sulfate
  5. customremoval of the solvent
  6. customthe residue was purified on a silica gel column chromatography (ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-809706498ec249afa17c75b700fcb6e6
Source dataset
uspto-grants-2006_06
Patent number
US07064119B2

Reaction notes

Loading…