Hydrazine → HCID 11370084, compound

HRID 1907955Notes

Reaction equation

HRID 1907955 reaction equation
NN.[NH2:3][C:4]1[C:13]2[N:14]=[C:15]([CH2:22][O:23][N:24]3C(=O)C4C(=CC=CC=4)C3=O)[N:16]([CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])[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]([CH2:22][O:23][NH2:24])[N:16]([CH2:17][C:18]([CH3:20])([OH:21])[CH3:19])[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 67052342HCID 67052342, compound

Product 1

HCID 11370084HCID 11370084, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Hydrazine (20 mL) was added to a stirred suspension of 2-{[4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methoxy}-1H-isoindole-1,3(2H)-dione (14.0 g, 32.4 mmol) in ethanol (100 mL). The mixture was stirred at room temperature and after 5 minutes a solution formed. After 1 hour, a solid began to form and additional ethanol (100 mL) was added. After 4.5 hours, the solid was isolated by filtration, washed with dichloromethane, and dried to yield 9.30 g of 1-{4-amino-2-[(aminooxy)methyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol as a yellow solid, some of which was used without further purification in the next step. Two batches of the product (6.63 g and 1.00 g) were purified by chromatography using a HORIZON HPFC system (silica gel, gradient elution with 5-15% of 2 M NH3 in methanol/chloroform) to provide 4.45 g and 650 mg of 1-{4-amino-2-[(aminooxy)methyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol as a yellow solid, respectively. Some of the chromatographed product (650 mg) was crystallized from acetonitrile to yield 377 mg of 1-{4-amino-2-[(aminooxy)methyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol as pale yellow crystals, mp 178-179° C.

Workup

  1. customformed
  2. waitAfter 1 hour
  3. customto form
  4. waitAfter 4.5 hours
  5. customthe solid was isolated by filtration
  6. washwashed with dichloromethane
  7. customdried

Sources & evidence

ORD record
ord-8728712445b34fd6ba21b4090000fc0f
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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