HCID 66926092, compound → HCID 66926124, compound

HRID 2170794Notes

Reaction equation

HRID 2170794 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH3:13])[N:10]([CH:14]3[C:18](=[O:19])/[C:17](=[CH:20]/[CH:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)/[CH2:16][C:15]3=[O:27])[N:9]=2)=[CH:4][CH:3]=1.[H][H]>CO.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH3:13])[N:10]([CH:14]3[C:18](=[O:19])[CH:17]([CH2:20][CH:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH2:16][C:15]3=[O:27])[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 66926092HCID 66926092, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66926124HCID 66926124, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-[3-(4-chloro-phenyl)-5-methyl-pyrazol-1-yl]-4-[1-(tetrahydro-pyran-4-yl)-meth-(E)-ylidene]-cyclopentane-1,3-dione (9 mg, 0.02 mmol) in methanol (0.1 ml) was added 5% palladium on activated charcoal (1 mg) and the reaction stirred for 6 hours under 1.5 bar of hydrogen. The solution was then filtered through a pad of Celite, washed with methanol (10 ml) and concentrated in vacuo to give a white solid, which was purified by reverse phase preparative HPLC (eluting with acetonitrile/water) to give 2-[3-(4-chloro-phenyl)-5-methyl-pyrazol-1-yl ]-4-(tetrahydro-pyran-4-ylmethyl)-cyclopentane-1,3-dione (4 mg).

Workup

  1. filtrationThe solution was then filtered through a pad of Celite
  2. washwashed with methanol (10 ml)
  3. concentrationconcentrated in vacuo
  4. customto give a white solid, which
  5. customwas purified by reverse phase preparative HPLC (eluting with acetonitrile/water)

Sources & evidence

ORD record
ord-68bd9715399b429ca99ffa8e5e9534be
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Reaction notes

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