N,N-Dimethylaniline → HCID 21104340, compound

HRID 1010838Notes

Reaction equation

HRID 1010838 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 oxychlorideHCID 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). 57 microliters N,N-dimethylaniline (catalyst) were added and heated to 110° C. overnight. The excess phosphorous oxychloride was removed under vacuum, and the residue was treated with ice, and the product extracted with chloroform. The chloroform extract was dried over sodium sulfate (anh.) and the solvent was removed to give crude product. The product was purified by silica gel chromatography eluting with chloroform to give 36 mg of product (yield: 56%).

Workup

  1. customThe excess phosphorous oxychloride was removed under vacuum
  2. additionthe residue was treated with ice
  3. extractionthe product extracted with chloroform
  4. extractionThe chloroform extract
  5. dry with materialwas dried over sodium sulfate (anh.)
  6. customthe solvent was removed
  7. customto give crude product
  8. customThe product was purified by silica gel chromatography
  9. washeluting with chloroform

Sources & evidence

ORD record
ord-33e9e144c0f14e79973e22383375ecda
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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