HCID 19356998, compound → HCID 19357017, compound

HRID 377864Notes

Reaction equation

HRID 377864 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[C:24]([O:30][CH3:31])[CH:23]=3)[CH2:18][CH2:17]2)=[O:15])[C:7]([O:11][CH3:12])=[N:8][C:9]=1[CH3:10])(=[O:3])[CH3:2].[CH3:32][Mg+].[Br-]>O1CCCC1>[OH:3][C:1]([C:4]1[CH:5]=[C:6]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:23]=[C:24]([O:30][CH3:31])[CH:25]=[C:26]([O:28][CH3:29])[CH:27]=3)[CH2:18][CH2:17]2)=[O:15])[C:7]([O:11][CH3:12])=[N:8][C:9]=1[CH3:10])([CH3:32])[CH3:2]

Participants

4

Reactant 2

HCID 19356998HCID 19356998, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 19357017HCID 19357017, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-{(5-Acetyl-2-methoxy-6-methylpyridin-3-yl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine(214 mg, 0.50 mmol) was dissolved in tetrahydrofuran(10 ml) and CH3MgBr(0.50 ml, 1.50 mmol) was added slowly. The mixture solution was refluxed for 15 hrs and concentrated under the reduced pressure to remove the solvent and extracted with ethylacetate, dried and filtered. The resultant was purified by column chromatography(ethylacetate:hexane=1:2) to obtain the titled compound.

Workup

  1. temperatureThe mixture solution was refluxed for 15 hrs
  2. concentrationconcentrated under the reduced pressure
  3. customto remove the solvent
  4. extractionextracted with ethylacetate
  5. customdried
  6. filtrationfiltered
  7. customThe resultant was purified by column chromatography(ethylacetate:hexane=1:2)

Sources & evidence

ORD record
ord-a149b399817949cda3b6f8df044d2126
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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