Ammonium formate → HCID 66700111, compound

HRID 1910718Notes

Reaction equation

HRID 1910718 reaction equation
C(=O)(O[CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11](Br)[N:12]=2)[N:7]([C:15](=[O:17])[CH3:16])[C:6]([CH2:19]C2C=CC=CC=2)(C)[CH2:5]1)N.C([O-])=O.[NH4+:30].[H][H]>C(O)C.[C].[Pd]>[C:15]([N:7]1[C:8]2[C:13](=[N:12][CH:11]=[CH:10][CH:9]=2)[CH:4]([NH2:30])[CH2:5][CH:6]1[CH3:19])(=[O:17])[CH3:16]

Participants

6

Reactant 3

HCID 2723923Ammonium formateHCID 86664528HCID 86664528, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66700111HCID 66700111, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

[Step 3] 279 mg of the benzyl-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-1,5-naphthyridin-4-yl carbamate and 126 mg of ammonium formate were dissolved in 5 mL of ethanol followed by adding 112 mg of 10% palladium carbon and stirring for 6 hours under normal pressure in a hydrogen atmosphere at room temperature. Following completion of the reaction, the solution was filtered with celite and concentrated under reduced pressure. The resulting residue was neutralized with saturated sodium bicarbonate and extracted five times with chloroform. After washing with saturated brine and dehydrating with anhydrous sodium sulfate, the solution was concentrated under reduced pressure and the resulting residue was purified using silica gel chromatography (saturated ammonia/methanol:chloroform=1:10) to obtain 85 mg of 1-acetyl-4-amino-2-methyl-3,4-dihydro-2H-[1,5]naphthyridine in the form of a red solid (62%).

Workup

  1. customcompletion of the reaction
  2. filtrationthe solution was filtered with celite and
  3. concentrationconcentrated under reduced pressure
  4. extractionextracted five times with chloroform
  5. washAfter washing with saturated brine
  6. concentrationthe solution was concentrated under reduced pressure
  7. customthe resulting residue was purified

Sources & evidence

ORD record
ord-edd31d3ea15b49ef98c346d8d8a9cbfc
Source dataset
uspto-grants-2013_12
Patent number
US08604030B2

Reaction notes

Loading…