Dimethylformamide → HCID 53361078, compound

HRID 1023373Notes

Reaction equation

HRID 1023373 reaction equation
CN(C=O)C.[Cl:6][C:7]1[CH:8]=[C:9](/[CH:30]=[CH:31]/[C:32]([N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)=[O:33])[CH:10]=[C:11]([CH3:29])[C:12]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])=[CH:16][N:15]=1.[CH:40]([C:42]1[CH:49]=[CH:48][C:45]([CH2:46]Cl)=[CH:44][CH:43]=1)=[CH2:41].C([O-])([O-])=O.[K+].[K+]>O>[Cl:6][C:7]1[CH:8]=[C:9](/[CH:30]=[CH:31]/[C:32]([N:34]2[CH2:39][CH2:38][N:37]([CH2:46][C:45]3[CH:48]=[CH:49][C:42]([CH:40]=[CH2:41])=[CH:43][CH:44]=3)[CH2:36][CH2:35]2)=[O:33])[CH:10]=[C:11]([CH3:29])[C:12]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])=[CH:16][N:15]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 74126p-Vinylbenzyl chlorideHCID 67327134HCID 67327134, compound

Product 1

HCID 53361078HCID 53361078, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a DMF (7 mL) solution of (E)-3-[3-chloro-4-({5-[(2-chlorobenzyl)oxy]-pyridin-2-yl}oxy)-5-methylphenyl]-1-(piperazin-1-yl)prop-2-en-1-one (0.70 g) and 4-vinylbenzyl chloride (240 μL) was added K2CO3 (291 mg) at room temperature. After stirring at room temperature for 36 hours, to the reaction mixture was added water, and extracted with AcOEt. The organic layer was washed with water, saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1 to 0/1 and then AcOEt/MeOH=19/1) to give (E)-3-[3-chloro-4-({5-[(2-chlorobenzyl)oxy]pyridin-2-yl}oxy)-5-methylphenyl]-1-[4-(4-ethenylbenzyl)-piperazin-1-yl]prop-2-en-1-one as a colorless powder (0.73 g).

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with water, saturated aqueous NaCl
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1 to 0/1

Sources & evidence

ORD record
ord-e23c177fd03d4eae80b190916f6c5456
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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