Diisopropylethylamine → HCID 68867528, compound

HRID 494104Notes

Reaction equation

HRID 494104 reaction equation
[Br:1][C:2]1[C:3](=[O:17])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:5]=[CH:6][C:7]=1Br.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][C:20]1=[O:25].C(N(C(C)C)CC)(C)C>C(O)C>[Br:1][C:2]1[C:3](=[O:17])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:5]=[CH:6][C:7]=1[N:22]1[CH2:23][CH2:24][N:19]([CH3:18])[C:20](=[O:25])[CH2:21]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 43990421-Methylpiperazin-2-oneHCID 31523025HCID 31523025, compound

Product 1

HCID 68867528HCID 68867528, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4,5-dibromo-2-(4-fluorobenzyl)pyridazin-3(2H)-one (0.8 g, 2.21 mmol), 1-methylpiperazin-2-one (0.33, 2.87 mmol; see Example 7, Step 3), and diisopropylethyl-amine (0.34 g, 3.32 mmol) in absolute ethanol (3 mL) was heated in a sealed tube in an oil bath at 100° C. overnight. The mixture was concentrated under vacuum. The residue was partitioned between ethyl acetate and brine. The organic extract was dried over sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluted with hexanes and ethyl acetate gradient to give titled material.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customThe residue was partitioned between ethyl acetate and brine
  3. extractionThe organic extract
  4. dry with materialwas dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. washeluted with hexanes and ethyl acetate gradient
  8. customto give titled material

Sources & evidence

ORD record
ord-62863e842c1640c499f2a7f613aa57ed
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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