Hydroxyamine hydrochloride → 4-cyclohexylamino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde oxime

HRID 1966811Notes

Reaction equation

HRID 1966811 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[CH:9]1([NH:15][C:16]2[C:21]([CH:22]=O)=[CH:20][N:19]=[C:18]3[N:24]([CH2:27][CH3:28])[N:25]=[CH:26][C:17]=23)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>C(O)C>[CH:9]1([NH:15][C:16]2[C:21]([CH:22]=[N:2][OH:3])=[CH:20][N:19]=[C:18]3[N:24]([CH2:27][CH3:28])[N:25]=[CH:26][C:17]=23)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 251057854-cyclohexylamino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde

Product 1

HCID 866475994-cyclohexylamino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (0.255 gm, 0.0036 mole) and sodium acetate (0.301 gm, 0.0036 mole) were added to a stirred solution of 4-(cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (0.250 gm, 0.0009 mole) (example 7) in ethanol. The reaction mixture was allowed to stir at room temperature for about 2 h. Ethanol was removed under reduced pressure and residue was poured in water. The title compound was then filtered and washed with water twice and finally with hexane.

Workup

  1. customEthanol was removed under reduced pressure and residue
  2. additionwas poured in water
  3. filtrationThe title compound was then filtered
  4. washwashed with water twice

Sources & evidence

ORD record
ord-83253dd701444a249c8a2608326454a3
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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