Hydrochloric Acid → HCID 70451362, compound

HRID 1623856Notes

Reaction equation

HRID 1623856 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:24]=[CH:23][C:22](/[CH:25]=[N:26]\O)=[CH:21][C:11]=2[C:12]([NH:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:13])=[CH:4][CH:3]=1.Cl.C(=O)([O-])O.[Na+].Cl[C:35]([O:37][CH3:38])=[O:36]>O1CCCC1.[Zn]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:24]=[CH:23][C:22]([CH2:25][NH:26][C:35](=[O:36])[O:37][CH3:38])=[CH:21][C:11]=2[C:12]([NH:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:13])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 516892Sodium Bicarbonate2×HCID 88593266HCID 88593266, compound

Product 1

HCID 70451362HCID 70451362, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-{[(4-fluorophenyl)methyl]oxy}-5-[(Z)-(hydroxyimino)methyl]-N-3-pyridinylbenzamide (may be prepared by Example 83; 215 mg, 0.57 mmol) in tetrahydrofuran (5 ml) was added 2M aqueous hydrochloric acid (1.72 ml, 56.7 mmol) followed by zinc (371 mg, 5.67 mmol) at room temperature. After stirring at room temperature for 30 min the mixture was heated to 60° C. for 30 min. On cooling, the mixture was treated with saturated sodium hydrogen carbonate (excess). A small amount of the solution was put aside to generate the amine. Methyl chloroformate (0.53 ml, 6.80 mmol) was added to the remainder and the pH was adjusted with further NaHCO3 to pH 9-10. The mixture was then stirred at room temperature for 1 hour. The tetrahydrofuran was evaporated under reduced pressure, and the resulting aqueous layer was extracted with ethyl acetate (2×30 ml), dried (MgSO4) and evaporated under reduced pressure. The residue was purified twice using MDAP to yield the title compound. 12 mg.

Workup

  1. temperaturewas heated to 60° C. for 30 min
  2. temperatureOn cooling
  3. stirringThe mixture was then stirred at room temperature for 1 hour
  4. customThe tetrahydrofuran was evaporated under reduced pressure
  5. extractionthe resulting aqueous layer was extracted with ethyl acetate (2×30 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. customThe residue was purified twice using MDAP

Sources & evidence

ORD record
ord-7952f63ef6df49d68cceb4456755efc0
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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