Triethylamine → N-(3-chloro-4-fluorophenyl)-4-methyl-3-(3-(pyridin-3-yl)acrylamido)benzamide

HRID 1968938Notes

Reaction equation

HRID 1968938 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[F:8].C([N:21](CC)CC)C.Cl.[N:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH:33]=[CH:34][C:35](Cl)=[O:36])[CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([NH:21][C:35](=[O:36])[CH:34]=[CH:33][C:29]3[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=3)[CH:12]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 710613N-(3-chloro-4-fluorophenyl)-4-methylbenzamideHCID 713600273-(3-Pyridyl)acryloyl chloride hydrochloride

Product 1

HCID 67493954N-(3-chloro-4-fluorophenyl)-4-methyl-3-(3-(pyridin-3-yl)acrylamido)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of step 2 (0.7 g) and anhydrous triethylamine (0.7 ml) in dichloromethane (20 ml), 3-pyridin-3-ylacryloyl chloride hydrochloride (1.2 g) was added in batches in an ice-bath with the temperature no more than 5° C. After addition, the reaction was carried out for 30 min in an ice-bath, and then at room temperature overnight. The completion of reaction was indicated by TLC. Then potassium carbonate solution (10%) was added. The mixture was extracted with EtOAc (20 ml*3). The organic layer was dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to recover solvent. The residue was purified on silica gel column using EtOAc/petroleum ether/ethanol (2:1:5) as an eluent. The concentration of the eluent and crystallization provided a yellow solid powder.

Workup

  1. additionAfter addition
  2. customat room temperature
  3. customovernight
  4. customThe completion of reaction
  5. extractionThe mixture was extracted with EtOAc (20 ml*3)
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto recover solvent
  10. customThe residue was purified on silica gel column
  11. customThe concentration of the eluent and crystallization
  12. customprovided a yellow solid powder

Sources & evidence

ORD record
ord-060b604547e84a518c211e752622f346
Source dataset
uspto-grants-2013_04
Patent number
US08426446B2

Reaction notes

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