Sodium Chloride → Methyl [6-[3-[4-(diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[1,5-b]pyridazin-7-yl]carboxylate

HRID 1169100Notes

Reaction equation

HRID 1169100 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[C:27]([C:35]([O:37][CH3:38])=[O:36])=[CH:28][C:29]2[N:30]([N:32]=[CH:33][N:34]=2)[N:31]=1.C(N(C(C)C)C(C)C)C.[Cl-].[Na+]>CN(C)C=O.O>[CH3:38][O:37][C:35]([C:27]1[C:26]([NH:18][CH2:17][CH2:16][CH2:15][N:12]2[CH2:13][CH2:14][CH:9]([O:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:10][CH2:11]2)=[N:31][N:30]2[N:32]=[CH:33][N:34]=[C:29]2[CH:28]=1)=[O:36]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamineHCID 56997997Methyl (6-chloro[1,2,4]triazolo[1,5-b]pyridazin-7-yl)carboxylate

Product 1

HCID 53760718Methyl [6-[3-[4-(diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[1,5-b]pyridazin-7-yl]carboxylateYield 41.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

1.42 g of 4-(diphenylmethoxy)-1-piperidinepropanamine and 929 mg of methyl (6-chloro[1,2,4]triazolo[1,5-b]pyridazin-7-yl)carboxylate were dissolved in 20 ml of N,N-dimethylformamide; 1.51 ml of N-ethyldiisopropylamine was added, followed by stirring at 70° C. for 6 hours. After cooling, water was added; the mixture was saturated with sodium chloride and extracted with ethyl acetate-tetrahydrofuran (1:1); the extract was dried over magnesium sulfate and 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; the residue was crystallized by the addition of ethyl acetate-ethyl ether-hexane (1:2:1), collected by filtration, washed with hexane and dried to yield 905 mg of the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate-tetrahydrofuran (1:1)
  3. dry with materialthe extract was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluted with ethyl acetate:methanol:triethylamine (50:5:1)
  6. customThe desired fraction was collected
  7. concentrationconcentrated
  8. customthe residue was crystallized by the addition of ethyl acetate-ethyl ether-hexane (1:2:1)
  9. filtrationcollected by filtration
  10. washwashed with hexane
  11. customdried

Sources & evidence

ORD record
ord-4f303efdd70347568df6beedc89effe3
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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