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Hydrochloric Acid → 1-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-2,2,2-trifluoro-1-(quinolin-6-yl)ethanol

HRID 69275
Notes
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Reaction equation

HRID 69275 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]=[CH:18][CH:17]=[CH:16]4)=[O:12])=[CH:9][N:10]=2)[N:7]=1.[F:23][C:24]([Si](C)(C)C)([F:26])[F:25].[F-].[K+].Cl>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]=[CH:18][CH:17]=[CH:16]4)([OH:12])[C:24]([F:26])([F:25])[F:23])=[CH:9][N:10]=2)[N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 86630275(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanone

Product 1

HCID 866351161-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-2,2,2-trifluoro-1-(quinolin-6-yl)ethanol

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-quinolin-6-yl-methanone (Stage 1.2, 50 mg, 0.162 mmol) was dissolved in DMF (5 mL) and (trifluoromethyl)trimethylsilane (1.294 mL, 8.10 mmol) and KF (4.70 mg, 0.081 mmol) were introduced. After 30 min at rt, 1 N HCl was added to the RM. It was stirred at rt for 20 h. the reaction was not completed. It was then heated at 150° C. under microwave irradiations for 5 min. It was extracted with EtOAc twice. Combined organic layers was washed with brine and dried over Na2SO4. It was filtered and the solvent was removed to afford as brown solid 1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-2,2,2-trifluoro-1-(quinolin-6-yl)ethanol (tR 0.8 min (conditions 2), MH+=379).

Workup

  1. temperatureIt was then heated at 150° C. under microwave irradiations for 5 min
  2. extractionIt was extracted with EtOAc twice
  3. washCombined organic layers was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationIt was filtered
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-b348cfc2f0864184af2134e181030c88
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822468B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes