HCID 19357135, compound → HCID 19357144, compound

HRID 377912Notes

Reaction equation

HRID 377912 reaction equation
[CH3:1][N:2]([C:21]1[C:22]([O:31][CH3:32])=[N:23][C:24]([CH3:30])=[C:25]([C:27](=[O:29])[CH3:28])[CH:26]=1)[C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH3:20])[CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[CH3:33][Mg]Br>O1CCCC1>[OH:29][C:27]([C:25]1[CH:26]=[C:21]([N:2]([CH3:1])[C:3]([N:5]2[CH2:6][CH2:7][N:8]([C:11]3[CH:12]=[C:13]([O:19][CH3:20])[CH:14]=[C:15]([O:17][CH3:18])[CH:16]=3)[CH2:9][CH2:10]2)=[O:4])[C:22]([O:31][CH3:32])=[N:23][C:24]=1[CH3:30])([CH3:33])[CH3:28]

Participants

4

Reactant 2

HCID 19357135HCID 19357135, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 19357144HCID 19357144, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[N-Methyl-N-(5-acetyl-2-methoxy-6-methylpyridin-3-yl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine(221 mg, 0.5 mmol) was dissolved in tetrahydrofuran(10 ml) and thereto methyl magnesium bromide(0.50 ml, 1.50 mmol). The resulting mixture was refluxed for 15 hrs, concentrated under the reduced pressure to remove used solvent, extracted with ethylacetate, filtered to dryness, and purified by column chromatography(ethylacetate:hexane=1:2) to obtain the titled compound.

Workup

  1. temperatureThe resulting mixture was refluxed for 15 hrs
  2. concentrationconcentrated under the reduced pressure
  3. customto remove
  4. extractionextracted with ethylacetate
  5. filtrationfiltered to dryness
  6. custompurified by column chromatography(ethylacetate:hexane=1:2)

Sources & evidence

ORD record
ord-d70c3374648c48ab9a6d7d0b80f00377
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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