Hydrazine → HCID 69078740, compound

HRID 244817Notes

Reaction equation

HRID 244817 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:22][O:23][CH2:24][CH3:25])[N:14]([CH2:15][CH2:16][CH2:17][O:18][CH:19]([CH3:21])[CH3:20])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:26][CH2:27][CH2:28][CH2:29][N:30]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:5][C:4]=2[N:3]=1.NN>C(O)C>[NH2:30][CH2:29][CH2:28][CH2:27][CH2:26][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[N:14]([CH2:15][CH2:16][CH2:17][O:18][CH:19]([CH3:20])[CH3:21])[C:13]([CH2:22][O:23][CH2:24][CH3:25])=[N:12][C:11]=3[C:2]([NH2:1])=[N:3][C:4]=2[CH:5]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 69081930HCID 69081930, compound

Product 1

HCID 69078740HCID 69078740, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-{4-[4-amino-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-7-yl]butyl}-1H-isoindole-1,3(2H)-dione (1.15 g, 2.1 mmol) was dissolved in ethanol (36 mL. Hydrazine (0.372 mL, 11.4 mmol) was added and the solution was heated at reflux temperature for 1 hour. The resulting white slurry was cooled to ambient temperature and filtered. The solid showed 40% product by NMR. The solid was saved and used in Part E. The filtrate was concentrated under reduced pressure and purified using a HORIZON HPFC system (silica cartridge, eluting with a linear gradient of 2-20% CMA in chloroform) to provide 0.211 g of 7-(4-aminobutyl)-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine as a white solid.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux temperature for 1 hour
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. custompurified
  6. washeluting with a linear gradient of 2-20% CMA in chloroform)

Sources & evidence

ORD record
ord-1e90d1ecd8164e6895a1651588ba5a78
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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