HCID 53763966, compound → HCID 53861570, compound

HRID 1839471Notes

Reaction equation

HRID 1839471 reaction equation
[C:1]([Cu])#[N:2].Br[C:5]1[CH:6]=[C:7]([CH:28]=[CH:29][C:30]=1[F:31])[C:8]([NH:10][C:11]1[C:12]([NH:17][C:18](=[O:27])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:9]>CN1C(=O)CCC1.C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[C:7]([CH:28]=[CH:29][C:30]=1[F:31])[C:8]([NH:10][C:11]1[C:12]([NH:17][C:18](=[O:27])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:9])#[N:2]

Participants

5

Reactant 2

HCID 53763966HCID 53763966, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 53861570HCID 53861570, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

CuCN (606 mg, 6.77 mmol) was dissolved in NMP (25 mL) and the solution was heated to 200° C. for 45 min. To this stirring solution was added N1-(3-bromo-4-fluorobenzoyl)-N2-(4-methoxybenzoyl)-1,2-benzenediamine (700 mg, 2.26 mmol) and stirring continued for 20 h. The solution was then cooled to room temperature, diluted with ethyl acetate and washed once with 1 N ammonium hydroxide, twice with 1 N HCl and once with brine. The organic phase was then dried with MgSO4, filtered and concentrated in vacuo. The residue was chromatographed with 10% ethyl acetate/dichloromethane to give 270 mg (44%) of off-white solid.

Workup

  1. temperatureThe solution was then cooled to room temperature
  2. washwashed once with 1 N ammonium hydroxide, twice with 1 N HCl and once with brine
  3. dry with materialThe organic phase was then dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed with 10% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-e5bb156f709748af8c1beaf791cf151b
Source dataset
uspto-grants-2004_01
Patent number
US06677369B2

Reaction notes

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