Diisopropylethylamine → HCID 59242671, compound

HRID 1630467Notes

Reaction equation

HRID 1630467 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:15]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(N(C(C)C)CC)(C)C>C(#N)C>[C:18]([O:17][C:15]([N:22]1[CH2:27][CH2:26][N:25]([C:5]2[N:4]=[N:3][C:2]([Cl:1])=[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:6]=2)[CH2:24][CH2:23]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 143452tert-Butyl piperazine-1-carboxylate2×HCID 113220803,6-Dichloro-4-phenylpyridazine

Product 1

HCID 59242671HCID 59242671, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 3,6-dichloro-4-phenyl-pyridazine (0.41 g, 1.82 mmol), prepared by following the procedure described in WO-2005/013907, N-Boc-piperazine (0.509 g, 2.73 mmol) and diisopropylethylamine (0.634 ml, 3.64 mmol) in acetonitrile (7.5 ml) was stirred at 180° C. for 40 min., under microwave irradiation, and then for a further 30 min. After this period, additional amounts of diisopropylethylamine (0.1 ml, 0.57 mmol) and N-Boc-piperazine (0.1 g, 0.54 mmol) were added and the resulting mixture was stirred at 180° C. for 40 min. The solvent was evaporated in vacuo and then, dichloromethane and a saturated solution of ammonium chloride were added. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The residue was then purified by column chromatography (silica gel; dichloromethane and heptane/ethyl acetate 8:2 to 7:3). The desired fractions were collected and evaporated in vacuo to yield D13 (0.137 g, 20%) as a white solid. C19H23ClN4O2 requires 374; Found 375 (MH+).

Workup

  1. customprepared
  2. waitfor a further 30 min
  3. waitAfter this period
  4. stirringthe resulting mixture was stirred at 180° C. for 40 min
  5. customThe solvent was evaporated in vacuo
  6. additiondichloromethane and a saturated solution of ammonium chloride were added
  7. customThe organic layer was separated
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customthe solvent evaporated in vacuo
  11. customThe residue was then purified by column chromatography (silica gel; dichloromethane and heptane/ethyl acetate 8:2 to 7:3)
  12. customThe desired fractions were collected
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-0b95c5aa1c5249c1ae5c52b30ea33b00
Source dataset
uspto-grants-2014_07
Patent number
US08791120B2

Reaction notes

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