Acetic Acid → HCID 57929920, compound

HRID 1930065Notes

Reaction equation

HRID 1930065 reaction equation
Br[CH:2]([C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:19]([CH:22]([CH3:24])[CH3:23])=[N:20][N:21]=2)[N:18]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[F:12])=O.[C:25]([N:29]1[CH2:34][CH2:33][CH:32]([C:35](=[S:37])[NH2:36])[CH2:31][CH2:30]1)([CH3:28])([CH3:27])[CH3:26].CC(O)=O>CN(C=O)C>[C:25]([N:29]1[CH2:30][CH2:31][CH:32]([C:35]2[S:37][C:2]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([C:19]([CH:22]([CH3:24])[CH3:23])=[N:20][N:21]=4)[N:18]=3)=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=3[F:12])[N:36]=2)[CH2:33][CH2:34]1)([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 579298612-Bromo-1-(2,4-difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanoneHCID 57929945HCID 57929945, compound

Product 1

HCID 57929920HCID 57929920, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 2-bromo-1-(2,4-difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (0.276 g, 0.699 mmol, Preparation #A.2), 1-tert-butylpiperidine-4-carbothioamide (0.140 g, 0.699 mmol) and HOAc (0.080 mL, 1.40 mmol) were added to DMF (4 mL). The mixture was stirred at ambient temperature for about 1 h then at about 85° C. for about 1.5 h. The reaction was cooled to ambient temperature and then concentrated under reduced pressure. The residue was partitioned between EtOAc and 1 N aqueous NaOH. The organic solution was dried over MgSO4, filtered and concentrated under reduced pressure to an oil which was then purified by flash chromatography on silica gel using DCM/MeOH with 3% NH4OH (95:5) as an eluent to give the title compound: (0.077 g, 22%): LC/MS (Table 1, Method a) Rt=1.66 min; MS m/z: 497.2 (M+H)+.

Workup

  1. waitat about 85° C. for about 1.5 h
  2. temperatureThe reaction was cooled to ambient temperature
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between EtOAc and 1 N aqueous NaOH
  5. dry with materialThe organic solution was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure to an oil which
  8. customwas then purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-1c1731e1ec9043c9809e931608069b99
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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