1,2-Dichloroethane → HCID 131723394, compound

HRID 1839459Notes

Reaction equation

HRID 1839459 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([NH:9][C:10]2[C:11]([NH2:16])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1.[F:19][C:20]1[CH:28]=[C:27]([C:29]#[N:30])[CH:26]=[CH:25][C:21]=1[C:22](O)=[O:23].C(N(CC)C(C)C)(C)C.C(Cl)CCl>CN(C=O)C>[F:19][C:20]1[CH:28]=[C:27]([C:29]#[N:30])[CH:26]=[CH:25][C:21]=1[C:22]([NH:16][C:11]1[C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:18][CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:23]

Participants

6

Reactant 4

HCID 111,2-Dichloroethane2×HCID 81531DiisopropylethylamineHCID 5906594-Cyano-2-fluorobenzoic acid2×HCID 785232N-(2-Aminophenyl)-4-methoxybenzamide

Product 1

HCID 131723394HCID 131723394, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N1-(4-methoxybenzoyl)-1,2-benzenediamine (0.5 g, 1.8 mmol), 2-fluoro-4-cyanobenzoic acid (0.3 g, 1.8 mmol) and N,N-diisopropylethylamine (0.23 g, 1.8 mmol) in DMF (5 mL) was added EDC (0.42 g, 2.2 mmol). After 48 h, 2-fluoro-4-cyanobenzoic acid (0.3 g, 1.8 mmol) and EDC (0.35 g, 1.8 mmol) were added. After an additional 24 h, the reaction was concentrated; and the residue was dissolved in ethyl acetate, washed with 1 N citric acid, brine, satd aq NaHCO3 and brine. The organic layer was MgSO4 dried, crystallized, filtered with ether wash, and dried under vacuum to give the title compound as a white solid 280 mg (40%); MS(FD): 389.1

Workup

  1. waitAfter an additional 24 h
  2. concentrationthe reaction was concentrated
  3. dissolutionand the residue was dissolved in ethyl acetate
  4. washwashed with 1 N citric acid, brine
  5. customdried
  6. customcrystallized
  7. filtrationfiltered with ether
  8. washwash
  9. customdried under vacuum

Sources & evidence

ORD record
ord-62461b466cc84eb083d9f418e48a57c7
Source dataset
uspto-grants-2004_01
Patent number
US06677369B2

Reaction notes

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