Diisopropylethylamine → HCID 9933860, compound

HRID 397576Notes

Reaction equation

HRID 397576 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8](=[O:11])[NH:9][N:10]=2)[N:7]=1.[C:12]1([CH:18]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:19][CH:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][NH2:29])[CH2:22][CH2:21]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(C(C)C)C(C)C)C>C(O)CCC>[C:30]1([CH:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:19][CH:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][NH:29][C:2]3[CH:3]=[CH:4][C:5]4[N:6]([C:8](=[O:11])[NH:9][N:10]=4)[N:7]=3)[CH2:22][CH2:21]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 64071826-chloro-2H,3H-[1,2,4]triazolo[4,3-b]pyridazin-3-oneHCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamine

Product 1

HCID 9933860HCID 9933860, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

0.512 g of 6-chloro[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one was dissolved in 15 ml of n-butanol; 0.88 g of 4-(diphenylmethoxy)-1-piperidinepropanamine and 1.04 ml of N-ethyldiisopropylamine were added, followed by refluxing under heating in an oil bath for 5 hours. After cooling, the n-butanol was mostly distilled off under reduced pressure; to the residue, an aqueous solution of sodium hydrogen carbonate was added; the reaction mixture was extracted with ethyl acetate; the extract was washed with saturated saline and dried over magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography and eluted with ethyl acetate-methanol-triethylamine (85:15:1). The desired fraction was collected and concentrated; the crystal obtained was filtered, washed with diethyl ether, and dried, to yield 0.35 g of the title compound.

Workup

  1. temperatureby refluxing
  2. temperatureunder heating in an oil bath for 5 hours
  3. temperatureAfter cooling
  4. distillationthe n-butanol was mostly distilled off under reduced pressure
  5. additionto the residue, an aqueous solution of sodium hydrogen carbonate was added
  6. extractionthe reaction mixture was extracted with ethyl acetate
  7. washthe extract was washed with saturated saline
  8. dry with materialdried over magnesium sulfate
  9. concentrationAfter concentration under reduced pressure
  10. washeluted with ethyl acetate-methanol-triethylamine (85:15:1)
  11. customThe desired fraction was collected
  12. concentrationconcentrated
  13. customthe crystal obtained
  14. filtrationwas filtered
  15. washwashed with diethyl ether
  16. customdried

Sources & evidence

ORD record
ord-d6a41b5460834f0abb7dc58704f5da83
Source dataset
uspto-grants-2003_08
Patent number
US06610694B1

Reaction notes

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