Ammonia → 3-[6-(Piperidin-1-yl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]benzamide

HRID 346505Notes

Reaction equation

HRID 346505 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([C:16]4[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=4)[C:19]([OH:21])=O)=[N:14][N:15]=3)[N:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[N:26](C=O)C.C(Cl)(=O)C(Cl)=O.N>C1COCC1>[N:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([C:16]4[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=4)[C:19]([NH2:26])=[O:21])=[N:14][N:15]=3)[N:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 231158963-[6-(Piperidin-1-yl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]benzoic acid

Product 1

HCID 231158883-[6-(Piperidin-1-yl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution mixture of 3-[6-(piperidin-1-yl)-1,2,4-triazolo[4,3-b]pyridazine-3-yl]benzoic acid (430 mg), a catalytic amount of DMF and THF (10 ml), oxalyl chloride (0.44 ml) was added with cooling in ice, and the mixture was stirred at room temperature for 2 hours and then ammonia gas was passed with cooling in ice for 15 minutes. The reaction solution was concentrated under reduced pressure, and the resultant residue was combined with chloroform:methanol (10:1), and then insoluble materials were filtered off. The filtrate was concentrated under reduced pressure, and the resultant crude crystals were recrystallized from ethanol to obtain 3-[6-(piperidin-1-yl)-1,2,4-triazolo[4,3-b]pyridazin-3-yl]benzamide (242 mg) as slightly tan crystals.

Workup

  1. temperaturewith cooling in ice
  2. temperaturewith cooling in ice for 15 minutes
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. filtrationinsoluble materials were filtered off
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe resultant crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-aa8166651746400fb809dc0e03524c20
Source dataset
uspto-grants-2007_02
Patent number
US07173033B2

Reaction notes

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