Diisopropylethylamine → 1-[3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-one

HRID 1675010Notes

Reaction equation

HRID 1675010 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=2)[N:7]=1.Cl.O.[NH:17]1[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]1.CCN(C(C)C)C(C)C>CN(C=O)C>[F:12][C:11]([F:14])([F:13])[C:8]1[N:6]2[N:7]=[C:2]([N:17]3[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]3)[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6136576-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazineHCID 2723901Piperonylamine

Product 1

HCID 595783691-[3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-oneYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

6-Chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (10.0 g, 44.93 mmol), 4-piperidone monohydrate hydrochloride (8.48 g, 49.43 mmol) and DIPEA (16.3 mL, 98.85 mmol) in DMF (100 mL) were stirred and heated at 90° C. for 1 hour. The DMF was then evaporated in vacuo and the residue purified by flash silica chromatography, eluting with 2% MeOH in DCM. Pure fractions were concentrated to give a pale yellow precipitate. The precipitate was collected by filtration, washed with ether and air dried to afford 1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-one (10.61 g, 83%) as a pale yellow solid.

Workup

  1. customThe DMF was then evaporated in vacuo
  2. customthe residue purified by flash silica chromatography
  3. washeluting with 2% MeOH in DCM
  4. concentrationPure fractions were concentrated
  5. customto give a pale yellow precipitate
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with ether and air
  8. customdried

Sources & evidence

ORD record
ord-13d39adcd7b14903a9ed68ddde45bb49
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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