HCID 18182411, compound → HCID 18182434, compound

HRID 1359319Notes

Reaction equation

HRID 1359319 reaction equation
[CH2:1]([C:8]1[C:9]([O:23][CH3:24])=[N:10][CH:11]=[C:12]([N:14](C(OC(C)(C)C)=O)[CH3:15])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[CH2:1]([C:8]1[C:9]([O:23][CH3:24])=[N:10][CH:11]=[C:12]([NH:14][CH3:15])[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 18182411HCID 18182411, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 18182434HCID 18182434, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

920 mg of 3-benzyl-5-(N-methyl-tert-butoxycarbonylamino)-2-methoxypyridine was dissolved in 5 ml of ethyl acetate, followed by adding 10 ml of 4N hydrochloric acid/ethyl acetate thereto. The resulting solid (640 mg) was collected by filtration. To the solid (230 mg) were added 10 ml of ethyl acetate, 150 mg of benzoyl chloride and 0.5 ml of pyridine in an ice bath, followed by stirring. After adding water thereto, the mixture was extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid, aqueous saturated sodium hydrogencarbonate and brine, dried over anhydrous magnesium sulfate and then evaporated, to give 270 mg of the target compound.

Workup

  1. filtrationThe resulting solid (640 mg) was collected by filtration
  2. additionTo the solid (230 mg) were added 10 ml of ethyl acetate, 150 mg of benzoyl chloride and 0.5 ml of pyridine in an ice bath
  3. additionAfter adding water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with 1N hydrochloric acid, aqueous saturated sodium hydrogencarbonate and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-0b05e85a507c45498980a06f8618b1f8
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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