Trifluoroacetic acid → HCID 25145649, compound

HRID 80716Notes

Reaction equation

HRID 80716 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[C:14]([CH3:17])[C:13]([N:18]4[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]4)=[N:12][N:11]3[C:31]=2[C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[C:14]([CH3:17])[C:13]([N:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)=[N:12][N:11]3[C:31]=2[C:32]2[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 59406949HCID 59406949, compound

Product 1

HCID 25145649HCID 25145649, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.43 g (0.86 mmol) of tert-butyl 4-[2-(4-fluorophenyl)-7,8-dimethyl-3-pyrid-4-ylimidazo[1,2-b]pyridazin-6-yl]piperazine-1-carboxylate in 5 mL of dichloromethane at 0° C. is added dropwise 0.64 mL (8.6 mmol) of trifluoroacetic acid. After stirring for 4 hours at room temperature, a further 0.64 mL (8.6 mmol) of trifluoroacetic acid is added and the reaction mixture is left for 18 hours. The solvent is then removed under reduced pressure and the residue is taken up in water. The resulting aqueous phase is washed with ether and then basified by addition of aqueous sodium hydrogen carbonate solution. The product is extracted with dichloromethane, the organic phase is dried over sodium sulfate and filtered, and the solvent is evaporated off to give 0.285 g of a white powder.

Workup

  1. waitthe reaction mixture is left for 18 hours
  2. customThe solvent is then removed under reduced pressure
  3. washThe resulting aqueous phase is washed with ether
  4. additionbasified by addition of aqueous sodium hydrogen carbonate solution
  5. extractionThe product is extracted with dichloromethane
  6. dry with materialthe organic phase is dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-ad1d2d21c1d54d0abdfa09c68e1567ee
Source dataset
uspto-grants-2014_09
Patent number
US08846676B2

Reaction notes

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