Dimethylformamide → HCID 66760157, compound

HRID 1850397Notes

Reaction equation

HRID 1850397 reaction equation
[CH2:1](I)[CH3:2].CN(C=O)C.[OH:9][C:10]1[C:18]2[O:17][C:16]([CH3:20])([CH3:19])[C:15](=[O:21])[C:14]=2[C:13]([CH3:22])=[C:12]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[CH2:25][CH2:24]2)[C:11]=1[CH3:37].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[CH2:1]([O:9][C:10]1[C:18]2[O:17][C:16]([CH3:19])([CH3:20])[C:15](=[O:21])[C:14]=2[C:13]([CH3:22])=[C:12]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[CH2:25][CH2:24]2)[C:11]=1[CH3:37])[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 66759872HCID 66759872, compound

Product 1

HCID 66760157HCID 66760157, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl iodide (88 mg, 0.567 mmol) was added to a suspension of DMF (4 mL) containing 7-hydroxy-5-[4-(4-methoxyphenyl)piperazin-1-yl]-2,2,4,6-tetramethyl-1-benzofuran-3(2H)-one (150 mg, 0.378 mmol) synthesized in Reference Example 73 and potassium carbonate (104 mg, 0.756 mmol) at 0° C. The reaction solution was warmed to room temperature and stirred for 15 hours. The resulting mixture was poured into water and extraction was performed using ethyl acetate. The extract was washed with saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5 to 80/20), and recrystallized from ethyl acetate and hexane to give 70 mg of the title compound (yield: 44%).

Workup

  1. washThe extract was washed with saturated saline
  2. customdried
  3. concentrationfollowed by concentration under reduced pressure
  4. customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5 to 80/20)
  5. customrecrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-ae05f429f4ca4f5fb0ae915ea3921a16
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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