Ethylenediamine → 2,3-Dihydro-5(4fluorophenyl)-6-(pyridin-4-yl)pyrazine

HRID 982913Notes

Reaction equation

HRID 982913 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=O)=[CH:4][CH:3]=1.[NH2:18][CH2:19][CH2:20][NH2:21]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[N:21][CH2:20][CH2:19][N:18]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 117909921-(4-Fluorophenyl)-2-(4-pyridinyl)-1,2-ethanedione

Product 1

HCID 225616712,3-Dihydro-5(4fluorophenyl)-6-(pyridin-4-yl)pyrazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

The compound, 1-(4-Fluorophenyl)-2-(pyridin-4-yl)ethanedione, the procedure of which may be found in U.S. Pat. No. 5,656,644, Example 13(b) whose disclosure is incorporated herein by reference in its entirety, (0.2 g, 0.87 mmol), and 1,2-diaminoethane (0.1 g, 1.67 mmol) were dissolved in methylene chloride (1 mL) and stirred under argon at 23° C. for about 12 hours. The solvent was removed in vacuo and the residue was chromatographed on silica gel eluted with 1-3% methanol in methylene chloride. Recrystallization from methylene chloride hexane gave the title compound as an yellow crystalline solid. ES (+) MS m/e=254 (MH+)

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was chromatographed on silica gel
  3. washeluted with 1-3% methanol in methylene chloride
  4. customRecrystallization from methylene chloride hexane

Sources & evidence

ORD record
ord-fd1432401b264252b27eb5af001c20d6
Source dataset
uspto-grants-2005_03
Patent number
US06861417B2

Reaction notes

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