Diisopropylethylamine → HCID 46681952, compound

HRID 1674761Notes

Reaction equation

HRID 1674761 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.Cl[C:24]1[CH:29]=[CH:28][C:27]2=[N:30][N:31]=[C:32]([C:33]([F:36])([F:35])[F:34])[N:26]2[N:25]=1>C(O)C>[F:35][C:33]([F:34])([F:36])[C:32]1[N:26]2[N:25]=[C:24]([N:4]3[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]3)[CH:29]=[CH:28][C:27]2=[N:30][N:31]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 6136576-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazine

Product 1

HCID 46681952HCID 46681952, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

A mixture of tert-butyl piperazine-1-carboxylate (8.29 g, 44.5 mmol) and ethanol (90 mL) was added to a mixture of diisopropylethylamine (9.16 mL, 52.6 mmol) and 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[3,4-f]pyridazine (9.0 g, 40.4 mmol) in ethanol (90 mL) The mixture was heated at 70° C. for 11 hours and then allowed to cool to ambient temperature to give a precipitate. The precipitate was collected by filtration, washed with chilled ethanol and then with water, and dried under vacuum to afford tert-butyl 4-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperazine-1-carboxylate (13.64 g, 90.6%) as a white solid that was used without further purification.

Workup

  1. temperatureto cool to ambient temperature
  2. customto give a precipitate
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with chilled ethanol
  5. dry with materialwith water, and dried under vacuum

Sources & evidence

ORD record
ord-f624fcb9c56149c5abe45f976275e51e
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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