Diisopropylethylamine → HCID 59242655, compound

HRID 1630472Notes

Reaction equation

HRID 1630472 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[N:10]=[N:9][C:8]=2[C:19]([F:22])([F:21])[F:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[C:30]([F:32])[CH:31]=1)[CH2:27]Br.C(N(C(C)C)CC)(C)C>C(#N)C>[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[C:30]([F:32])[CH:31]=1)[CH2:27][N:16]1[CH2:15][CH2:14][N:13]([C:11]2[N:10]=[N:9][C:8]([C:19]([F:22])([F:21])[F:20])=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:12]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5188963,5-Difluorobenzyl bromideHCID 24880031HCID 24880031, compound

Product 1

HCID 59242655HCID 59242655, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-phenyl-6-piperazin-1-yl-3-trifluoromethyl-pyridazine (E1) (0.050 g, 0.16 mmol), 3,5-difluorobenzyl bromide (0.031 ml, 0.24 mmol) and diisopropylethylamine (0.056 ml, 0.32 mmol) in acetonitrile (2 ml) was stirred at 100° C. for 10 min., under microwave irradiation. The solvent was evaporated in vacuo and then, dichloromethane and ammonium chloride (10% aqueous solution) were added. The mixture was filtered through a diatomaceous earth cartridge. The solvent was then evaporated in vacuo and the residue was purified by CC-TLC (centrifugal circular thin-layer chromatography) on a chromatotron (a preparative, centrifugally accelerated, radial, thin-layer chromatograph). The crude product was crystallised from diethyl ether/heptane to yield E3 (0.037 g, 52%) as a solid. C22H19F5N4 requires 434; Found 435 (MH+).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additiondichloromethane and ammonium chloride (10% aqueous solution) were added
  3. filtrationThe mixture was filtered through a diatomaceous earth cartridge
  4. customThe solvent was then evaporated in vacuo
  5. customthe residue was purified by CC-TLC (centrifugal circular thin-layer chromatography) on a chromatotron (a preparative,
  6. customThe crude product was crystallised from diethyl ether/heptane

Sources & evidence

ORD record
ord-14538d9e14e44d719055dadf3f7cab65
Source dataset
uspto-grants-2014_07
Patent number
US08791120B2

Reaction notes

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