Acetonitrile → HCID 86629831, compound

HRID 1907957Notes

Reaction equation

HRID 1907957 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:24][O:25]N)[N:18]([CH2:19][C:20]([CH3:23])([OH:22])[CH3:21])[C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1.C(#[N:29])C>CN(C=O)C>[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:24][O:25][N:2]([CH3:1])[C:3]([NH2:29])=[O:4])[N:18]([CH2:19][C:20]([OH:22])([CH3:23])[CH3:21])[C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 12228Methyl IsocyanateHCID 11370084HCID 11370084, compound

Product 1

HCID 86629831HCID 86629831, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl isocyanate (0.148 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). A solid formed immediately. The mixture was stirred for 2 hours at room temperature, then was heated to form a solution to which acetonitrile (10 mL) was added. Crystals formed that were isolated by filtration and purified by chromatography using a HORIZON HPFC (silica gel, gradient elution with 5-20% 2 M NH3 in methanol/chloroform). The appropriate fractions were combined and concentrated to a solid that was dried in a vacuum oven overnight to afford N-{[4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methoxy}-N-methylurea as white crystals, mp 206-207° C.

Workup

  1. customA solid formed immediately
  2. temperaturewas heated
  3. additionwas added
  4. customCrystals formed
  5. customthat were isolated by filtration
  6. custompurified by chromatography
  7. washa HORIZON HPFC (silica gel, gradient elution with 5-20% 2 M NH3 in methanol/chloroform)
  8. concentrationconcentrated to a solid
  9. customthat was dried in a vacuum oven overnight

Sources & evidence

ORD record
ord-c86eb1a0fe4b44cb868bc5d4b983644a
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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