HCID 89709123, compound → HCID 117667473, compound

HRID 1526204Notes

Reaction equation

HRID 1526204 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH:12]=2)=[CH:5][C:4]([NH2:14])=[N:3]1>[Pd].C(O)C>[CH3:1][N:2]1[C:6]([CH:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12]2)=[CH:5][C:4]([NH2:14])=[N:3]1

Participants

4

Reactant 1

HCID 89709123HCID 89709123, compound

Product 1

HCID 117667473HCID 117667473, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 1-methyl-5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrazol-3-amine (574 mg) and ethanol (10 mL) was added 10% palladium-supported carbon (50% wet product) (318 mg), followed by stirring for 5 hours under a hydrogen gas atmosphere (4 atm). The reaction mixture was filtered through celite and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH2 type, eluent; chloroform:methanol=100:0-95:5), and the obtained solid was washed with diisopropyl ether:ethyl acetate (10:1) to obtain 1-methyl-5-(1-methylpiperidin-4-yl)-1H-pyrazol-3-amine (367 mg) as a colorless solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent was evaporated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (NH2 type, eluent; chloroform:methanol=100:0-95:5)
  4. washthe obtained solid was washed with diisopropyl ether:ethyl acetate (10:1)

Sources & evidence

ORD record
ord-395029abacda4c1089dd914351884aba
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

Loading…