Triethylamine → HCID 22633003, compound

HRID 2270246Notes

Reaction equation

HRID 2270246 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[F:13][C:14]1[CH:15]=[C:16]([NH2:24])[C:17](=[CH:21][C:22]=1[F:23])[C:18]([OH:20])=O.Cl.[CH2:26]([O:29][NH2:30])[CH:27]=[CH2:28].C(N(CC)CC)C>C1COCC1>[NH2:24][C:16]1[CH:15]=[C:14]([F:13])[C:22]([F:23])=[CH:21][C:17]=1[C:18]([NH:30][O:29][CH2:26][CH:27]=[CH2:28])=[O:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 7359652-Amino-4,5-difluorobenzoic acidHCID 3084724O-Allylhydroxylamine hydrochloride

Product 1

HCID 22633003HCID 22633003, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbonyldiimidazole (3.37 g, 20 mmol) was added to a suspension of 4,5-difluoroanthranilic acid (3.0 g, 17 mmol) in 80 mL of THF, and the mixture was heated to reflux for 2 hours. The solution was cooled and O-allylhydroxylamine hydrochloride (1.89 g, 17 mmol) and triethylamine (2.8 mL, 20 mmol) were added, and the mixture was heated to reflux for 17 hours. The reaction mixture was concentrated and washed with 1N HCl, saturated NaHCO3, and brine and dried over magnesium sulfate. The solution was concentrated and purified by column chromatography (silica gel, CHCl3/MeOH, 98:2) to give 2.08 g of the title compound as a solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe solution was cooled
  4. temperaturethe mixture was heated
  5. temperatureto reflux for 17 hours
  6. concentrationThe reaction mixture was concentrated
  7. washwashed with 1N HCl, saturated NaHCO3, and brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationThe solution was concentrated
  10. custompurified by column chromatography (silica gel, CHCl3/MeOH, 98:2)

Sources & evidence

ORD record
ord-42664aa8c5f64180be6047cd23c6fb86
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

Loading…