Hydrazine → HCID 57515603, compound

HRID 44799Notes

Reaction equation

HRID 44799 reaction equation
NN.[NH2:3][C:4]1[C:13]2[N:14]=[C:15]([CH2:23][N:24]3C(=O)C4C(=CC=CC=4)C3=O)[N:16]([CH2:17][C:18]3([OH:22])[CH2:21][CH2:20][CH2:19]3)[C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=1>C(O)C>[NH2:3][C:4]1[C:13]2[N:14]=[C:15]([CH2:23][NH2:24])[N:16]([CH2:17][C:18]3([OH:22])[CH2:21][CH2:20][CH2:19]3)[C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 57515602HCID 57515602, compound

Product 1

HCID 57515603HCID 57515603, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, hydrazine (0.89 mL, 28 mmol) was added to a suspension of 2-({4-amino-1-[(1-hydroxycyclobutyl)methyl]-1H-imidazo[4,5-c]quinolin-2-yl}methyl)-1H-isoindole-1,3(2H)-dione (2.42 g, 5.66 mmol) in ethanol (57 mL), and the reaction was stirred for two hours at room temperature. The ethanol was removed under reduced pressure, and the resulting white solid was triturated with 2 N hydrochloric acid. The resulting suspension was filtered to remove a solid, and the filter cake was washed with water. The filtrate was made basic with the addition of solid sodium bicarbonate. A precipitate formed and was isolated by filtration, washed with water, and dried at 50° C. for three days in a vacuum oven to provide 0.994 g of 1-{[4-amino-2-(aminomethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclobutanol as a yellow solid.

Workup

  1. customThe ethanol was removed under reduced pressure
  2. customthe resulting white solid was triturated with 2 N hydrochloric acid
  3. filtrationThe resulting suspension was filtered
  4. customto remove a solid
  5. washthe filter cake was washed with water
  6. additionThe filtrate was made basic with the addition of solid sodium bicarbonate
  7. customA precipitate formed
  8. customwas isolated by filtration
  9. washwashed with water
  10. customdried at 50° C. for three days in a vacuum oven

Sources & evidence

ORD record
ord-03e00ae7817945c39f20c03923f2b37c
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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