Hydrochloric Acid → HCID 13749197, compound

HRID 1732002Notes

Reaction equation

HRID 1732002 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)=[CH:6][N:5]=[C:4]2[N:17]([CH2:20][CH3:21])[N:18]=[CH:19][C:3]=12.Cl.[NH2:23]O.Cl>C(O)(=O)C>[CH2:20]([N:17]1[C:4]2[N:5]=[CH:6][C:7]3[C:2](=[N:23][O:16][C:8]=3[C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=3)[C:3]=2[CH:19]=[N:18]1)[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 14171316HCID 14171316, compound

Product 1

HCID 13749197HCID 13749197, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Chloro-1-ethyl-5-(3-fluorobenzoyl)-1H-pyrazolo[3,4-b]pyridine (4.60 g) and hydroxylamine hydrochloride (14.0 g) were refluxed in a solution of 250 ml of acetic acid and 4 ml of concentrated hydrochloric acid. After 90 minutes, the solvent was evaporated and the residue distributed between dichloromethane and an aqueous sodium bicarbonate solution. The organic phase was evaporated and the residue was chromatographed over 230-400 mesh silica gel (10% ethyl acetate/dichloromethane). Evaporation of the appropriate fractions gave 3.2 g of product, mp 182°-184°. Recrystallization from ethyl acetate gave analytically pure product, mp 183°-184° C.

Workup

  1. customthe solvent was evaporated
  2. customThe organic phase was evaporated
  3. customthe residue was chromatographed over 230-400 mesh silica gel (10% ethyl acetate/dichloromethane)
  4. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-445dbd926294492a86ea613573f55c75
Source dataset
uspto-grants-1986_11
Patent number
US04624955

Reaction notes

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