HCID 178471076, compound → ethyl 3-[4-(2-chlorophenyl)-5-cyano-2,4-dihydro-1H-pyrazolo[3,4-b]pyridin-6-yl]propanoate

HRID 489409Notes

Reaction equation

HRID 489409 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]#[N:15])=[C:12](/[CH:16]=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:11][C:10]2=[N:23][NH:24][CH:25]=[C:9]12>[Pd].C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]#[N:15])=[C:12]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:11][C:10]2=[N:23][NH:24][CH:25]=[C:9]12

Participants

4

Reactant 1

HCID 178471076HCID 178471076, compound

Product 1

HCID 178471078ethyl 3-[4-(2-chlorophenyl)-5-cyano-2,4-dihydro-1H-pyrazolo[3,4-b]pyridin-6-yl]propanoateYield 61.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 4-(2-chlorophenyl)-5-cyano-4,7-dihydro-6-(trans-2-ethoxycarbonylethenyl)-2H-pyrazolo[3,4-b]pyridine (260 mg) and 5% palladium on carbon (110 mg) in ethanol was subjected to catalytic hydrogenation at room temperature for 5 hours. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate (1:1)) to give a yellow solid. The yellow solid was crystallized from ethyl acetate-diisopropyl ether to give the title compound (160 mg) as pale-yellow crystals.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate (1:1))
  4. customto give a yellow solid
  5. customThe yellow solid was crystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-13b0b2f7300e4613b79e4751d1360db9
Source dataset
uspto-grants-2005_12
Patent number
US06977262B2

Reaction notes

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