Triethylamine → HCID 22105971, compound

HRID 1456369Notes

Reaction equation

HRID 1456369 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[C:4](C(O)=O)[C:3]1=[O:22].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.C([N:42]([CH2:45]C)CC)C.[F:47][C:48]1[CH:54]=[C:53]([F:55])[CH:52]=[CH:51][C:49]=1[NH2:50]>C1C=CC=CC=1>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[C:4]([NH:42][C:45]([NH:50][C:49]2[CH:51]=[CH:52][C:53]([F:55])=[CH:54][C:48]=2[F:47])=[O:30])[C:3]1=[O:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 97092,4-DifluoroanilineHCID 199401P,P-Diphenylphosphinic azideHCID 22106115HCID 22106115, compound

Product 1

HCID 22105971HCID 22105971, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1-methyl-4-(2-chlorophenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine-3-carboxylic acid (315 mg, 1 mmol), diphenylphosphoryl azide (330 mg, 1.2 mmol) and triethylamine (101 mg, 1 mmol) in benzene (4 ml) was stirred at room temperature for 0.5 hour, and then refluxed for 0.5 hour. After allowed to stand for cooling, to the mixture was added 2,4-difluoroaniline (152 mg, 1.2 mmol), and the mixture was stirred at room temperature for 0.5 hour, and then stirred under reflux for two hours. After allowed to stand for cooling, the mixture was washed with water, washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting solid was recrystallized from isopropanol to give the title compound (288 mg, 0.65 mmol) as a colorless crystal.

Workup

  1. temperaturerefluxed for 0.5 hour
  2. temperaturefor cooling, to the mixture
  3. stirringstirred
  4. temperatureunder reflux for two hours
  5. temperaturefor cooling
  6. washthe mixture was washed with water
  7. washwashed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting solid was recrystallized from isopropanol

Sources & evidence

ORD record
ord-03e8b1287cfc49bbbd3347892a986c2c
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

Loading…