HCID 23365834, compound → Methyl 4-[6-(2-cyclopentylacetamido)-3-oxo-2-propyl-2H,3H-indazol-1-ylmethyl]-3-methoxybenzoate

HRID 1723248Notes

Reaction equation

HRID 1723248 reaction equation
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([NH:14][C:15](=[O:22])[CH2:16][CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:9][CH:10]=2)[N:5]1[CH2:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][C:25]=1[O:34][CH3:35])[CH:2]=[CH2:3]>C(OCC)(=O)C.[Pd]>[CH:17]1([CH2:16][C:15]([NH:14][C:8]2[CH:7]=[C:6]3[C:11]([C:12](=[O:13])[N:4]([CH2:1][CH2:2][CH3:3])[N:5]3[CH2:23][C:24]3[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][C:25]=3[O:34][CH3:35])=[CH:10][CH:9]=2)=[O:22])[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

4

Reactant 1

HCID 23365834HCID 23365834, compound

Product 1

HCID 23365844Methyl 4-[6-(2-cyclopentylacetamido)-3-oxo-2-propyl-2H,3H-indazol-1-ylmethyl]-3-methoxybenzoateYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Palladium-on-carbon (5% w/w, 0.095 g.) was added to a solution of methyl 4-[2-allyl-6-(2-cyclopentylacetamido)-3-oxo-2H,3H-indazol-1-ylmethyl]-3-methoxybenzoate (0.462 g.) in ethyl acetate (20 ml.). The mixture was hydrogenated at 1.1 bar for 5 hours. The catalyst was removed by filtration through diatomaceous earth, the filtrate evaporated and the residue purified by flash chromatography on silica gel (40 g.), eluting with 1:3:7 v/v/v acetic acid:ethyl acetate:dichloromethane. The chromatographed product was dissolved in acetone and toluene, and the solution evaporated to give the title compound in 84% yield, as a solid glass, m.p. 74.5°-77° C.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe filtrate evaporated
  3. customthe residue purified by flash chromatography on silica gel (40 g.)
  4. washeluting with 1:3:7 v/v/v acetic acid
  5. dissolutionThe chromatographed product was dissolved in acetone
  6. customtoluene, and the solution evaporated

Sources & evidence

ORD record
ord-35aab26d4b3b406596a512238acea6d7
Source dataset
uspto-grants-1989_08
Patent number
US04859692

Reaction notes

Loading…