HCID 57932938, compound → HCID 57932932, compound

HRID 1432675Notes

Reaction equation

HRID 1432675 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[S:8][C:9]([C:13]3[N:17]4[N:18]=[C:19]([CH3:27])[CH:20]=[C:21]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[C:16]4=[N:15][C:14]=3[CH3:28])=[C:10]([CH3:12])[N:11]=2)[CH2:3][CH2:2]1>[Pd].C(O)C>[CH2:23]([CH:22]([C:21]1[C:16]2[N:17]([C:13]([C:9]3[S:8][C:7]([CH:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)=[N:11][C:10]=3[CH3:12])=[C:14]([CH3:28])[N:15]=2)[N:18]=[C:19]([CH3:27])[CH:20]=1)[CH2:25][CH3:26])[CH3:24]

Participants

4

Reactant 1

HCID 57932938HCID 57932938, compound

Product 1

HCID 57932932HCID 57932932, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Add 3-[2-(3,6-dihydro-2H-pyran-4-yl)-4-methyl-thiazol-5-yl]-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (55 mg, 0.14 mmol), 5% palladium on carbon (55 mg) and absolute ethanol (50 ml) to a pressure vessel. Purge the reaction vessel with nitrogen, purge the reaction vessel with hydrogen, pressurize the reaction mixture with hydrogen (415 KPa), seal the vessel, agitate the reaction and heat to 40° C. Continue the reaction for 18 hours then turn off the heat and allow the reaction mixture to cool to ambient temperature. Vent the excess hydrogen from the vessel and purge the vessel with nitrogen. Filter the reaction mixture to remove the 5% palladium on carbon. The filtrate is concentrated and applied onto a silica-gel chromatography column (Hexane:AcOEt:2 M NH3 in MeOH=10:3:1) to give 12.8 mg of the title compound. Yield 23%. mass spectrum (m/e): 399 (M+1). 1H NMR (CDCl3): δ 6.73 (s, 1H), 4.14 (m, 2H), 3.60 (m, 2H), 3.34 (m, 2H), 2.56 (s, 3H), 2.48 (s, 3H), 2.36 (s, 3H), 2.16 (m, 2H), 2.02 (m, 2H), 1.87 (m, 4H), 0.91 (t, J=7.6 Hz, 6H).

Workup

  1. customPurge the reaction vessel with nitrogen
  2. custompurge the reaction vessel with hydrogen
  3. customseal the vessel
  4. customthe reaction
  5. customthe reaction for 18 hours
  6. temperatureheat
  7. temperatureto cool to ambient temperature
  8. customVent the excess hydrogen from the vessel and purge the vessel with nitrogen
  9. filtrationFilter the reaction mixture
  10. customto remove the 5% palladium on carbon
  11. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-1772eea879fd45a790fe195b43ed4816
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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