HCID 58899623, compound → HCID 178464758, compound

HRID 2246622Notes

Reaction equation

HRID 2246622 reaction equation
[CH2:1]([NH:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([C:12]2[CH:20]=[C:19]3[C:15]([C:16]([C:21]4[CH2:22][CH2:23][NH:24][CH2:25][CH:26]=4)=[N:17][NH:18]3)=[CH:14][CH:13]=2)[CH:6]=1)[CH3:2]>C(O)C.CN(C=O)C.[Pd]>[CH2:1]([NH:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([C:12]2[CH:20]=[C:19]3[C:15]([C:16]([CH:21]4[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]4)=[N:17][NH:18]3)=[CH:14][CH:13]=2)[CH:6]=1)[CH3:2]

Participants

5

Reactant 1

HCID 58899623HCID 58899623, compound2×

Product 1

HCID 178464758HCID 178464758, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-ethyl-4-methyl-3-[3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indazol-6-yl]benzamide (Intermediate 15, 360 mg) in ethanol (10 ml) and DMF (3 ml) was stirred with 10% palladium on carbon (50 mg) under an atmosphere of hydrogen for 24 h. The catalyst was removed by filtration, the solvent was evaporated and the residue was dissolved in methanol and applied to an SCX ion exchange cartridge. The cartridge was eluted with a solution of aqueous ammonia (0.88) in methanol (10%) and the resultant product was further purified on a column of silica, eluting with a dichloromethane/methanol gradient, to give the title compound (210 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated
  3. dissolutionthe residue was dissolved in methanol
  4. washThe cartridge was eluted with a solution of aqueous ammonia (0.88) in methanol (10%)
  5. customthe resultant product was further purified on a column of silica
  6. washeluting with a dichloromethane/methanol gradient

Sources & evidence

ORD record
ord-41b5dc4a771c4eb1860bc2304538e4b1
Source dataset
uspto-grants-2010_03
Patent number
US07687532B2

Reaction notes

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