Sodium Bicarbonate → 6-[5-[4-(Diphenylmethoxy)piperidino]pentylamino][1,2,4]triazolo[1,5-b]pyridazine

HRID 1067562Notes

Reaction equation

HRID 1067562 reaction equation
[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:28]1[CH:29]=[CH:30][C:31]2[N:32]([N:34]=[CH:35][N:36]=2)[N:33]=1.C(=O)(O)[O-].[Na+]>>[C:1]1([CH:7]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:28]3[CH:29]=[CH:30][C:31]4[N:32]([N:34]=[CH:35][N:36]=4)[N:33]=3)[CH2:11][CH2:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 112406116-Chloro-(1,2,4)triazolo(1,5-b)pyridazineHCID 229893744-(Diphenylmethoxy)-1-piperidinepentanamine

Product 1

HCID 229892706-[5-[4-(Diphenylmethoxy)piperidino]pentylamino][1,2,4]triazolo[1,5-b]pyridazineYield 66.9%

Procedure

0.705 g of 4-(diphenylmethoxy)-1-piperidinepentanamine and 0.309 g of 6-chloro[1,2,4]triazolo[1,5-b]pyridazine were stirred at 135-140° C. for 1.5 hours. After cooling, aqueous sodium bicarbonate was added, followed by extraction with ethyl acetate; the extract was washed with saline and dried with sodium 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 (95:5:1). The desired fraction was collected, recrystallized from ethyl ether and dried to yield 0.629 g of the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe extract was washed with saline
  4. dry with materialdried with sodium sulfate
  5. concentrationThe dry product was concentrated under reduced pressure
  6. washeluted with ethyl acetate:methanol:triethylamine (95:5:1)
  7. customThe desired fraction was collected
  8. customrecrystallized from ethyl ether
  9. customdried

Sources & evidence

ORD record
ord-c0f34e4b203b43e493438b7e220edd07
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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