Triethylamine → HCID 59519503, compound

HRID 1161827Notes

Reaction equation

HRID 1161827 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-85e2c9c7fc74458ca6bd6dda204f0686
Source dataset
uspto-grants-2010_10
Patent number
US07820664B2

Reaction notes

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