Triethylamine → 3-(1-Methanesulfonylpiperidin-3-yl)-6-piperidin-1-yl-1,2,4-triazolo[4,3-b]pyridazine

HRID 346503Notes

Reaction equation

HRID 346503 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH:16]4[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]4)=[N:14][N:15]=3)[N:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl>[CH3:29][S:30]([N:18]1[CH2:19][CH2:20][CH2:21][CH:16]([C:13]2[N:11]3[N:12]=[C:7]([N:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)[CH:8]=[CH:9][C:10]3=[N:15][N:14]=2)[CH2:17]1)(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 230579466-Piperidin-1-yl-3-piperidin-3-yl-1,2,4-triazolo[4,3-b]pyridazine

Product 1

HCID 230579623-(1-Methanesulfonylpiperidin-3-yl)-6-piperidin-1-yl-1,2,4-triazolo[4,3-b]pyridazineYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution mixture of 6-piperidin-1-yl-3-piperidin-3-yl-1,2,4-triazolo[4,3-b]pyridazine (670 mg), triethylamine (360 mg) and methylene chloride (15 ml), methanesulfonyl chloride (320 mg) was added and the mixture was stirred at room temperature for 8 hours. The reaction solution was concentrated under reduced pressure, and the resultant residue was extracted with ethyl acetate. The extract was washed successively with water and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resultant crude crystals were recrystallized from ethanol to obtain 3-(1-methanesulfonylpiperidin-3-yl)-6-piperidin-1-yl-1,2,4-triazolo[4,3-b]pyridazine (230 mg) as colorless crystals.

Workup

  1. additionwas added
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. extractionthe resultant residue was extracted with ethyl acetate
  4. washThe extract was washed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-54a8e83216f44d0e9bb2fa0427ef1e2f
Source dataset
uspto-grants-2007_02
Patent number
US07173033B2

Reaction notes

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