Triethylamine → HCID 67494121, compound

HRID 1968940Notes

Reaction equation

HRID 1968940 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[NH:11][C:12](=[O:21])[CH:13]=[CH:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH:27][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([NH:11][C:12](=[O:21])[CH:13]=[CH:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:4]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 97314-FluoroanilineHCID 11430Potassium CarbonateHCID 123547368HCID 123547368, compound

Product 1

HCID 67494121HCID 67494121, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of the product of step 3 (0.3 g) in anhydrous dichloromethane (30 ml), a solution of 4-fluoroaniline (0.1 g) and triethylamine (0.2 ml) in dichloromethane (15 ml) was added dropwise slowly 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. Potassium carbonate solution (10%) was added. The reaction 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 a silica gel column using EtOAc/petroleum ether/ethanol (1:2:0.5) as an eluent. The concentration of the eluent and crystallization provided a solid powder.

Workup

  1. additionAfter addition
  2. customat room temperature
  3. customovernight
  4. customThe completion of reaction
  5. extractionThe reaction 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 a silica gel column
  11. customThe concentration of the eluent and crystallization
  12. customprovided a solid powder

Sources & evidence

ORD record
ord-9ea2d68e87014752a1c4813f62446a03
Source dataset
uspto-grants-2013_04
Patent number
US08426446B2

Reaction notes

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