Hydrochloric Acid → HCID 13749198, compound

HRID 1732003Notes

Reaction equation

HRID 1732003 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][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][C:12]([F:15])=[CH:11][CH:10]=3)[C:3]=2[CH:19]=[N:18]1)[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 14171317HCID 14171317, compound

Product 1

HCID 13749198HCID 13749198, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Chloro-1-ethyl-5-(4-fluorobenzoyl)-1H-pyrazolo[3,4-b]pyridine (4.5 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 two hours the solvent was evaporated and the residue distributed between dichloromethane and an aqueous sodium bicarbonate solution. The organic phase was evaporated and the residue chromatographed over 230-400 mesh silica gel (10% ethyl acetate/dichloromethane). Evaporation of the appropriate fractions gave 2.2 g of product after trituration with pentane, mp 222°-223° C.

Workup

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

Sources & evidence

ORD record
ord-4e74fffa55cb4084a8a96c085aef6ad6
Source dataset
uspto-grants-1986_11
Patent number
US04624955

Reaction notes

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