Hydrochloric Acid → HCID 58869099, compound

HRID 1623205Notes

Reaction equation

HRID 1623205 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH3:29])[N:14]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]([O:27][CH3:28])[C:20]([NH:22][Si](C)(C)C)=[O:21])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.Cl>O1CCCC1>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH3:29])[N:14]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]([O:27][CH3:28])[C:20]([NH2:22])=[O:21])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86612267HCID 86612267, compound

Product 1

HCID 58869099HCID 58869099, compoundYield 7.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[4-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N-methoxy-N′-(trimethylsilyl)urea (4.1 g, 9.9 mmol) in tetrahydrofuran (75 mL) was added 10% aqueous HCl (5 mL). The reaction mixture was stirred at room temperature for two hours. The reaction mixture was concentrated under reduced pressure and the residue was neutralized with saturated aqueous sodium bicarbonate. The mixture was extracted with 10% methanol/dichloromethane solution. The organic layer was concentrated under reduced pressure and the crude product was recrystallized twice from methanol. The crystals were dissolved in hot methanol, filtered through a micron filter, and concentrated under reduced pressure to afford a solid that was crystallized from 5% methanol in dichloromethane to yield 0.264 g of N-[4-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N-methoxyurea as a yellow powder, mp 158-160° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionThe mixture was extracted with 10% methanol/dichloromethane solution
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe crude product was recrystallized twice from methanol
  5. dissolutionThe crystals were dissolved in hot methanol
  6. filtrationfiltered through a micron
  7. filtrationfilter
  8. concentrationconcentrated under reduced pressure
  9. customto afford a solid
  10. customthat was crystallized from 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-29db4509f0bd4de48e206f3a58aed343
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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