Triethylamine → HCID 59519503, compound

HRID 558239Notes

Reaction equation

HRID 558239 reaction equation
[F:1][C:2]1[C:3]2[C:4](=[C:20]([CH3:23])[O:21][N:22]=2)[N:5]=[C:6](C(O)=O)[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=1[F:16].C([N:26]([CH2:29]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:38])C=CC=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[C:3]2=[N:22][O:21][C:20]([CH3:23])=[C:4]2[N:5]=[C:6]2[NH:26][C:29](=[O:38])[N:8]([C:9]3[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=3[F:16])[C:7]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 59519498HCID 59519498, compound

Product 1

HCID 59519503HCID 59519503, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 7-fluoro-6-(2-fluoro-4-iodophenylamino)-3-methylisoxazolo[4,3-b]pyridine-5-carboxylic acid (241 mg, 0.56 mmol) in toluene (10 ml) is added triethylamine (0.23 ml, 1.68 mmol) and diphenylphosphoryl azide (0.26 ml, 1.21 mmol). The reaction is heated at reflux for 4 h. The mixture is cooled to room temperature and concentrated to dryness. Silica gel chromatography yields the title compound.

Workup

  1. temperatureThe reaction is heated
  2. temperatureat reflux for 4 h
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3c42ccae9ddd4984a019729e47f303c8
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

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