Trifluoroacetic acid → 6-[4-[4-[2-(Piperazin-1-yl)ethoxy]phenyl]piperidin-1-yl]-3-(trifluoromethyl)-7,8-dihydro-[1,2,4]triazolo[4,3-b]pyridazine

HRID 2381095Notes

Reaction equation

HRID 2381095 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]([F:48])([F:47])[C:10]1[N:14]2[N:15]=[C:16]([N:19]3[CH2:24][CH2:23][CH:22]([C:25]4[CH:46]=[CH:45][C:28]([O:29][CH2:30][CH2:31][N:32]5[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]5)=[CH:27][CH:26]=4)[CH2:21][CH2:20]3)[CH2:17][CH2:18][C:13]2=[N:12][N:11]=1>C(Cl)Cl>[N:32]1([CH2:31][CH2:30][O:29][C:28]2[CH:45]=[CH:46][C:25]([CH:22]3[CH2:23][CH2:24][N:19]([C:16]4[CH2:17][CH2:18][C:13]5[N:14]([C:10]([C:9]([F:47])([F:48])[F:8])=[N:11][N:12]=5)[N:15]=4)[CH2:20][CH2:21]3)=[CH:26][CH:27]=2)[CH2:33][CH2:34][NH:35][CH2:36][CH2:37]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68503507Tert-butyl 4-[2-[4-[1-[3-(trifluoromethyl)-7,8-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperidin-4-yl]phenoxy]ethyl]piperazine-1-carboxylate

Product 1

HCID 685030846-[4-[4-[2-(Piperazin-1-yl)ethoxy]phenyl]piperidin-1-yl]-3-(trifluoromethyl)-7,8-dihydro-[1,2,4]triazolo[4,3-b]pyridazineYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (10 mL) was added to tert-butyl 4-[2-[4-[1-[3-(trifluoromethyl)-7,8-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperidin-4-yl]phenoxy]ethyl]piperazine-1-carboxylate (2.02 g, 3.50 mmol) in DCM (10 mL). The resulting solution was stirred at ambient temperature for 1 hour then added to an SCX column. The desired product was eluted from the column using 2M ammonia/MeOH and the solvents were evaporated to afford 6-[4-[4-[2-(piperazin-1-yl)ethoxy]phenyl]piperidin-1-yl]-3-(trifluoromethyl)-7,8-dihydro-[1,2,4]triazolo[4,3-b]pyridazine (1.660 g, 99%) as a solid.

Workup

  1. additionthen added to an SCX column
  2. washThe desired product was eluted from the column
  3. customthe solvents were evaporated

Sources & evidence

ORD record
ord-efc5b60ad7144d6e9bcede412a1280b6
Source dataset
uspto-grants-2012_09
Patent number
US08258140B2

Reaction notes

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