Diisopropylethylamine → HCID 54215311, compound

HRID 1067555Notes

Reaction equation

HRID 1067555 reaction equation
[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:26]1[CH:27]=[CH:28][C:29]2[N:30]([C:32]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:33]([CH3:35])[N:34]=2)[N:31]=1.C(N(C(C)C)C(C)C)C.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[C:19]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:26]3[CH:27]=[CH:28][C:29]4[N:30]([C:32]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:33]([CH3:35])[N:34]=4)[N:31]=3)[CH2:11][CH2:10]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamineHCID 14091884Ethyl 6-chloro-2-methylimidazo[1,2-b]pyridazine-3-carboxylate

Product 1

HCID 54215311HCID 54215311, compoundYield 12.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

1.98 g of 4-(diphenylmethoxy)-1-piperidinepropanamine and 1.46 g of ethyl (6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl]carboxylate were dissolved in 15 ml of 1-methyl-2-pyrrolidone; 1.05 ml of N-ethyldiisopropylamine was added, followed by stirring at 120° C. for 40 hours. After cooling, aqueous sodium bicarbonate was added, followed by extraction with ethyl acetate; the extract was washed with saturated saline and dried with magnesium sulfate. The dry product was concentrated under reduced pressure; the residue was subjected to silica gel column chromatography and eluted with ethyl acetate:methanol:triethylamine (50:5:1). The desired fraction was collected and concentrated; ethyl ether-hexane (1:2) was added to the residue; the crystal precipitated was collected by filtration, washed with hexane and dried to yield 412 mg of the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe extract was washed with saturated saline
  4. dry with materialdried with magnesium sulfate
  5. concentrationThe dry product was concentrated under reduced pressure
  6. washeluted with ethyl acetate:methanol:triethylamine (50:5:1)
  7. customThe desired fraction was collected
  8. concentrationconcentrated
  9. additionethyl ether-hexane (1:2) was added to the residue
  10. customthe crystal precipitated
  11. filtrationwas collected by filtration
  12. washwashed with hexane
  13. customdried

Sources & evidence

ORD record
ord-6a1bc9e1fa2c4c85af5057ba7a814f4c
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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