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

HRID 2381087Notes

Reaction equation

HRID 2381087 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]([F:49])([F:48])[C:10]1[N:14]2[N:15]=[C:16]([N:19]3[CH2:24][CH2:23][CH:22]([C:25]4[CH:47]=[CH:46][C:28]([O:29][CH2:30][CH2:31][CH2:32][N:33]5[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]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:33]1([CH2:32][CH2:31][CH2:30][O:29][C:28]2[CH:27]=[CH:26][C:25]([CH:22]3[CH2:21][CH2:20][N:19]([C:16]4[CH2:17][CH2:18][C:13]5[N:14]([C:10]([C:9]([F:49])([F:48])[F:8])=[N:11][N:12]=5)[N:15]=4)[CH2:24][CH2:23]3)=[CH:47][CH:46]=2)[CH2:34][CH2:35][NH:36][CH2:37][CH2:38]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68500212Tert-butyl 4-[3-[4-(1-[3-(trifluoromethyl)-7,8-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperidin-4-yl]phenoxy]propyl]piperazine-1-carboxylate

Product 1

HCID 685023596-[4-[4-[3-(Piperazin-1-yl)propoxy]phenyl]piperidin-1-yl]-3-(trifluoromethyl)-7,8-dihydro-[1,2,4]triazolo[4,3-b]pyridazineYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (10 mL) was added to tert-butyl 4-[3-[4-(1-[3-(trifluoromethyl)-7,8-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperidin-4-yl]phenoxy]propyl]piperazine-1-carboxylate (2.09 g, 3.53 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 in methanol and the solvents were evaporated to dryness to afford 6-[4-[4-[3-(piperazin-1-yl)propoxy]phenyl]piperidin-1-yl]-3-(trifluoromethyl)-7,8-dihydro-[1,2,4]triazolo[4,3-b]pyridazine (1.700 g, 98%) 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 to dryness

Sources & evidence

ORD record
ord-25862eb4764546b7b977a2cf2e19d4ca
Source dataset
uspto-grants-2012_09
Patent number
US08258140B2

Reaction notes

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