Triethylamine → HCID 117701583, compound

HRID 1507457Notes

Reaction equation

HRID 1507457 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(N(CC)CC)C.[CH3:17][O:18][CH2:19][O:20][C:21]1[C:30]([CH3:31])=[C:29]2[C:24]([C:25](=[O:37])[C:26]([CH3:36])=[C:27](S(C)(=O)=O)[O:28]2)=[CH:23][CH:22]=1.C(OCC)(=O)C>CS(C)=O>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:27]2[O:28][C:29]3[C:24]([C:25](=[O:37])[C:26]=2[CH3:36])=[CH:23][CH:22]=[C:21]([O:20][CH2:19][O:18][CH3:17])[C:30]=3[CH3:31])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 837951-AcetylpiperazineHCID 117701578HCID 117701578, compound

Product 1

HCID 117701583HCID 117701583, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-Acetylpiperazine (220 mg, 1.70 mmol) and triethylamine (1 mL) were added to a solution of 7-(methoxymethoxy)-3,8-dimethyl-2-(methylsulfonyl)-4H-chromen-4-one (171 mg, 0.55 mmol) obtained in Example 37-3 in dimethyl sulfoxide (5 mL), and the mixture was stirred for 5 hours under cooling with ice. Ethyl acetate was added to the reaction solution. The organic layer was washed with water and then dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=97/3→93/7) to obtain 60 mg of the title compound (yield: 30%), which was used directly in the next reaction.

Workup

  1. temperatureunder cooling with ice
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=97/3→93/7)

Sources & evidence

ORD record
ord-552a19a08b204192af20b0848bf44616
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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