N,N-Dimethylaniline → HCID 21104340, compound

HRID 1354306Notes

Reaction equation

HRID 1354306 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([C:8]2[NH:13][C:12](=O)[C:11]3=[CH:15][CH:16]=[CH:17][N:10]3[N:9]=2)[CH:7]=1.P(Cl)(Cl)([Cl:21])=O.CN(C)C1C=CC=CC=1>>[Cl:21][C:12]1[C:11]2=[CH:15][CH:16]=[CH:17][N:10]2[N:9]=[C:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[F:18])[N:13]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychloride2×HCID 136007996HCID 136007996, compound

Product 1

HCID 21104340HCID 21104340, compoundYield 56%

Conditions

Temperature
110 °C

Procedure

2-(5-Chloro-2-fluoro-phenyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (60 mg, 0.228 mmole) was added to phosphorous oxychloride (1 ml). Added 57 microliters N,N-dimethylaniline (catalyst) and heated to 110° C. overnight. Removed excess phosphorous oxychloride under vacuum, residue treated with ice, and product extracted with chloroform. Dried chloroform extract over sodium sulfate (anh.) and removed solvent to give crude product. Product was purified by silica gel chromatography eluted with chloroform to give 36 mg product (yield: 56%).

Workup

  1. extractionextracted with chloroform
  2. extractionDried chloroform extract over sodium sulfate (anh.)
  3. customremoved solvent
  4. customto give crude product
  5. customProduct was purified by silica gel chromatography
  6. washeluted with chloroform

Sources & evidence

ORD record
ord-a434a1d8eb4f4fdf906a169aecd17714
Source dataset
uspto-grants-2007_05
Patent number
US07223766B2

Reaction notes

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