Cesium carbonate → HCID 86701049, compound

HRID 715737Notes

Reaction equation

HRID 715737 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]2[N:13]=[C:14]([SH:17])[CH:15]=[CH:16][C:11]2=[N:10][N:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:25]([CH2:34][CH3:35])[C:26]([N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:27]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]2[N:13]=[C:14]([S:17][CH:25]([CH2:34][CH3:35])[C:26]([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:27])[CH:15]=[CH:16][C:11]2=[N:10][N:9]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 13036622HCID 13036622, compoundHCID 178505612HCID 178505612, compound

Product 1

HCID 86701049HCID 86701049, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine-6-thiol (1 mmol) and cesium carbonate (1.5 equiv.) in DMF (5 mL) was added 2-bromo-1-(piperidin-1-yl)butan-1-one (1.5 equiv.) and the mixture was stirred at 70° C. for 3 hours. The reaction was monitored by thin-layer chromatography and was shown to be complete at this time. The solvent was removed in vacuo and the residue was flash chromatographed to give 2-((3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)thio)-1-(piperidin-1-yl)butan-1-one.

Workup

  1. customThe solvent was removed in vacuo
  2. customchromatographed

Sources & evidence

ORD record
ord-ad82f8b989d8439399514c6fed5d99fa
Source dataset
uspto-grants-2015_11
Patent number
US09187484B2

Reaction notes

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