4-Fluorobenzylamine → HCID 54365091, compound

HRID 1107775Notes

Reaction equation

HRID 1107775 reaction equation
[CH2:1]([N:5]1[C:9]2=[C:10](Cl)[N:11]=[N:12][CH:13]=[C:8]2[C:7]([CH3:15])=[C:6]1[CH3:16])[CH:2]=[CH:3][CH3:4].[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1>>[CH2:1]([N:5]1[C:9]2=[C:10]([NH:23][CH2:22][C:21]3[CH:24]=[CH:25][C:18]([F:17])=[CH:19][CH:20]=3)[N:11]=[N:12][CH:13]=[C:8]2[C:7]([CH3:15])=[C:6]1[CH3:16])[CH:2]=[CH:3][CH3:4]

Participants

3

Reactant 2

HCID 673264-FluorobenzylamineHCID 537196241-(2-Butenyl)-7-chloro-2,3-dimethylpyrrolo[2,3-d]pyridazine

Product 1

HCID 54365091HCID 54365091, compound

Conditions

Temperature
180 °C

Procedure

A solution of 0.35 g (0.0015 mole) of 1-(2-butenyl)-7-choro-2,3-dimethylpyrrolo[2,3-d]pyridazine dissolved in 3.5 ml of 4-fluorobenzylamine was heated at 180° C. for 2.5 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature and then poured into ice-water. The aqueous mixture was extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography through silica gel using a 30:1 mixture of chloroform and methanol as an eluent to give 0.22 g of 1-(2-butenyl)-7-(4-fluorobenzylamino)-2,3-dimethylpyrrolo[2,3-d]pyridazine (cis/trans=1/4) as a flesh-colored powder.

Workup

  1. customAfter completion of the reaction
  2. temperatureto cool to room temperature
  3. extractionThe aqueous mixture was extracted with dichloromethane
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by column chromatography through silica gel using
  7. additiona 30:1 mixture of chloroform and methanol as an eluent

Sources & evidence

ORD record
ord-c1905e71c266401599719cb63c886cb2
Source dataset
uspto-grants-2000_05
Patent number
US06063782

Reaction notes

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