Water → HCID 19357152, compound

HRID 377866Notes

Reaction equation

HRID 377866 reaction equation
[OH:1][CH:2]([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])[CH3:3].CN(C1C=CC=CN=1)C.[C:41](O)(=[O:47])[CH2:42][CH2:43][C:44]([OH:46])=[O:45].O>N1C=CC=CC=1>[CH3:29][O:28][C:26]1[CH:27]=[C:22]([N:19]2[CH2:20][CH2:21][N:16]([C:14]([NH:13][C:6]3[CH:5]=[C:4]([CH:2]([O:1][C:41](=[O:47])[CH2:42][CH2:43][C:44]([OH:46])=[O:45])[CH3:3])[C:9]([CH3:10])=[N:8][C:7]=3[O:11][CH3:12])=[O:15])[CH2:17][CH2:18]2)[CH:23]=[C:24]([O:30][CH3:31])[CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1110Succinic AcidHCID 218852-DimethylaminopyridineHCID 19357063HCID 19357063, compound

Product 1

HCID 19357152HCID 19357152, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-{[5-(1-Hydroxyethyl)-2-methoxy-6-methylpyridin-3-yl]aminocarbonyl}-4-(3,5-dimethoxyphenyl)piperazine(107 mg, 0.25 mmol) and dimethylaminopyridine(3 mg, 0.025 mmol) were dissolved in pyridine and anhydrous succinic acid(50 mg, 0.5 mmol) was added. The mixture was stirred at room temperature for 5 hrs. Distilled water was added into the above mixture. The above solution was extracted with CH2Cl2 and the organic phase washed with 1N-HCl and then concentrated under the reduced pressure to remove the solvent. The concentrate was purified by column chromatography(dichloromethane:methanol=20:1) to obtain the titled compound.

Workup

  1. extractionThe above solution was extracted with CH2Cl2
  2. washthe organic phase washed with 1N-HCl
  3. concentrationconcentrated under the reduced pressure
  4. customto remove the solvent
  5. customThe concentrate was purified by column chromatography(dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-9a086c6a590f4f0ab6705fbd8fbdbdcc
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

Loading…