Water → HCID 11349685, compound

HRID 1907956Notes

Reaction equation

HRID 1907956 reaction equation
[CH:1]([N:4]=[C:5]=[O:6])([CH3:3])[CH3:2].[NH2:7][C:8]1[C:17]2[N:18]=[C:19]([CH2:26][O:27][NH2:28])[N:20]([CH2:21][C:22]([CH3:25])([OH:24])[CH3:23])[C:16]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1.O>CN(C=O)C>[NH2:7][C:8]1[C:17]2[N:18]=[C:19]([CH2:26][O:27][NH:28][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[N:20]([CH2:21][C:22]([OH:24])([CH3:25])[CH3:23])[C:16]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 61277Isopropyl isocyanate2×HCID 11370084HCID 11370084, compound

Product 1

HCID 11349685HCID 11349685, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Isopropyl isocyanate (0.234 mL, 2.39 mmol) was added to a stirred solution of 1-{4-amino-2-[(aminooxy)methyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol (prepared as described in Example 100, 600 mg, 1.99 mmol) in DMF (5 mL). After 5 minutes, a solid formed. The mixture was stirred for 1 hour and 45 minutes, then additional isopropyl isocyanate (0.234 mL) and DMF (2 mL) was added. The mixture was stirred at room temperature for 45 minutes. Water (40 mL) was added and a solid was isolated by filtration. The solid was washed with water and dried under vacuum to provide 272 mg of N-{[4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methoxy}-N′-isopropylurea as a white solid. The filtrate was allowed to stand overnight at room temperature and crystals formed. The crystals were isolated by filtration, washed with acetonitrile, and dried in a vacuum oven at 60° C. to afford additional 38 mg of N-{[4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methoxy}-N′-isopropylurea, as yellow crystals, mp 231-233° C.

Workup

  1. customa solid formed
  2. stirringThe mixture was stirred at room temperature for 45 minutes
  3. customa solid was isolated by filtration
  4. washThe solid was washed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-e4892cab598c4df5a6d88114e6f495c2
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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