Hydrazine → HCID 11208418, compound

HRID 1907966Notes

Reaction equation

HRID 1907966 reaction equation
NN.[NH2:3][C:4]1[C:13]2[N:14]=[C:15]([CH2:21][O:22][N:23]3C(=O)C4C(=CC=CC=4)C3=O)[N:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:12]=2[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[NH2:23][O:22][CH2:21][C:15]1[N:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:12]2[C:11]3[N:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]=[C:4]([NH2:3])[C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 10340Sodium CarbonateHCID 67052400HCID 67052400, compound

Product 1

HCID 11208418HCID 11208418, compoundYield 44.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Anhydrous hydrazine (0.640 mL, 20.2 mmol) was added to a suspension of 2-{[4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methoxy}-1H-isoindole-1,3(2H)-dione (2.81 g, 6.75 mmol) in ethanol (40 mL). Gradually, a solution formed from which a solid began to precipitate. The reaction mixture was stirred overnight at room temperature, then was concentrated under reduced pressure. The residue was triturated with 1 M aqueous hydrochloric acid (50 mL). The mixture was sonicated and the solid was isolated by filtration. The filtrate was adjusted to pH 8 with solid sodium carbonate and extracted with dichloromethane (3×25 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated to afford a yellow solid. The solid was triturated with methanol to afford 0.863 g of 2-[(aminooxy)methyl]-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine as a white powder.

Workup

  1. customGradually, a solution formed from which a solid
  2. customto precipitate
  3. concentrationwas concentrated under reduced pressure
  4. customThe residue was triturated with 1 M aqueous hydrochloric acid (50 mL)
  5. customThe mixture was sonicated
  6. customthe solid was isolated by filtration
  7. extractionextracted with dichloromethane (3×25 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto afford a yellow solid
  12. customThe solid was triturated with methanol

Sources & evidence

ORD record
ord-176203b1ff044fe1b8210e750b717966
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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