Trifluoroacetic acid → HCID 59149746, compound

HRID 1675081Notes

Reaction equation

HRID 1675081 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]([F:46])([F:45])[C:10]1[N:14]2[N:15]=[C:16]([N:19]3[CH2:24][CH2:23][CH:22]([C:25]4[C:33]5[C:28](=[CH:29][CH:30]=[C:31]([C:34]([N:36]6[CH2:41][CH2:40][N:39](C([O-])=O)[CH2:38][CH2:37]6)=[O:35])[CH:32]=5)[NH:27][CH:26]=4)[CH2:21][CH2:20]3)[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1>C(Cl)Cl>[N:36]1([C:34]([C:31]2[CH:32]=[C:33]3[C:28](=[CH:29][CH:30]=2)[NH:27][CH:26]=[C:25]3[CH:22]2[CH2:23][CH2:24][N:19]([C:16]3[CH:17]=[CH:18][C:13]4[N:14]([C:10]([C:9]([F:46])([F:8])[F:45])=[N:11][N:12]=4)[N:15]=3)[CH2:20][CH2:21]2)=[O:35])[CH2:37][CH2:38][NH:39][CH2:40][CH2:41]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86638080HCID 86638080, compound

Product 1

HCID 59149746HCID 59149746, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added in one portion at ambient temperature to a stirred solution of tert-butyl [4-[3-[1-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]-1H-indole-5-carbonyl]piperazine-1-carboxylate (190 mg, 0.32 mmol) in DCM (2 mL). The resulting solution was stirred for 1 hour then applied to an SCX column and eluted with MeOH followed by 2M ammonia in MeOH. Pure fractions were combined and concentrated by evaporation then triturated with ether to give a solid which was collected by filtration and air dried to give 6-[4-[5-(piperazin-1-ylcarbonyl)-1H-indol-3-yl]piperidin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (156 mg, 99%) as a colourless solid.

Workup

  1. washeluted with MeOH
  2. concentrationconcentrated by evaporation
  3. customthen triturated with ether
  4. customto give a solid which
  5. filtrationwas collected by filtration and air
  6. customdried

Sources & evidence

ORD record
ord-41c0714528b342a08e5c9513feb153a6
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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