Hydrochloric Acid → HCID 13290651, compound

HRID 1507622Notes

Reaction equation

HRID 1507622 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4](=[N:14]O)[C:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)=[O:6].[ClH:17]>CO>[ClH:17].[CH3:1][O:2][C:3](=[O:16])[CH:4]([NH2:14])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)=[O:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178501738HCID 178501738, compound

Product 1

HCID 13290651HCID 13290651, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of oxime 5 (18.0 g, 80.0 mmol) in MeOH (220 mL) was mixed with 1.25 M HCl solution in MeOH (130 mL) at rt. The solution was flushed with N2 and then charged with 5% Pd—C (3.1 g). A hydrogen balloon was attached to the flask and the resulting mixture was stirred at rt for 2.5 h. More 5% Pd-C (˜1.8 g every 2 h) was added as the reaction was carefully monitored by LCMS. Eventually, the reaction was completed in 8 h with totally 9.4 g of 5% Pd—C added. After Pd catalyst was removed by filtering through a Celite pad, the clear solution was concentrated under reduced pressure to afford hydrochloride salt of pure product 6 (20.0 g, 100%) as a white solid. ESI MS m/z 212.2 (M+H)+.

Workup

  1. customThe solution was flushed with N2
  2. additioncharged with 5% Pd—C (3.1 g)
  3. additionMore 5% Pd-C (˜1.8 g every 2 h) was added as the reaction
  4. waitEventually, the reaction was completed in 8 h with totally 9.4 g of 5% Pd—C
  5. additionadded
  6. customAfter Pd catalyst was removed
  7. filtrationby filtering through a Celite pad
  8. concentrationthe clear solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-45564d080dbf4a448bd82e1b3c5d3ff8
Source dataset
uspto-grants-2015_12
Patent number
US09221805B2

Reaction notes

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