Triethylamine → HCID 58869073, compound

HRID 1623201Notes

Reaction equation

HRID 1623201 reaction equation
[CH:1]([N:4]=[C:5]=[O:6])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl.[OH:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[C:33]2[C:32]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N:26]=[C:25]([NH2:34])[C:24]=2[N:23]=[C:22]1[CH2:35][CH2:36][CH3:37].[OH-].[Na+]>ClCCl>[NH2:34][C:25]1[C:24]2[N:23]=[C:22]([CH2:35][CH2:36][CH3:37])[N:21]([CH2:20][CH2:19][CH2:18][CH2:17][N:16]([OH:15])[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[C:33]=2[C:32]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N:26]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 61277Isopropyl isocyanateHCID 86612264HCID 86612264, compound

Product 1

HCID 58869073HCID 58869073, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isopropyl isocyanate (0.67 mL, 6.85 mmol) and triethylamine (2.38 mL, 17.1 mmol) were added to a solution of 1-[4-(hydroxyamino)butyl]-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride (prepared as described in Parts A-D of Example 43, 2.00 g, 5.71 mmol) in dichloromethane (50 mL). The reaction mixture was stirred at room temperature for 2 hours, then 10% aqueous sodium hydroxide (2 equivalents) was added. After the mixture was stirred for 1 hour at room temperature, the layers were separated and the organic layer was washed with saturated aqueous sodium bicarbonate and brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography (silica gel, eluted with 3% methanol in dichloromethane). The appropriate fractions were combined and concentrated under reduced pressure. The resulting solid was slurried in 1:1 saturated aqueous sodium bicarbonate/water and was isolated by filtration, washed with water, and dried overnight in a vacuum oven at 80° C. to provide 0.327 g of N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N-hydroxy-N′-isopropylurea as beige needles, mp 158-160° C.

Workup

  1. stirringAfter the mixture was stirred for 1 hour at room temperature
  2. customthe layers were separated
  3. washthe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (silica gel, eluted with 3% methanol in dichloromethane)
  8. concentrationconcentrated under reduced pressure
  9. customwas isolated by filtration
  10. washwashed with water
  11. customdried overnight in a vacuum oven at 80° C.

Sources & evidence

ORD record
ord-10f58ec40dc248cd8661696b872f2d5c
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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