Triethylamine → HCID 58833647, compound

HRID 540959Notes

Reaction equation

HRID 540959 reaction equation
Cl.Cl.[NH2:3][C:4]1[C:13]2[N:14]=[C:15]([CH2:22][O:23][CH2:24][CH3:25])[N:16]([CH2:17][C:18]([CH3:21])([OH:20])[CH3:19])[C:12]=2[C:11]2[CH:10]=[CH:9][C:8]([O:26][CH2:27][CH2:28][NH2:29])=[CH:7][C:6]=2[N:5]=1.C(N(CC)CC)C.[CH:37]([N:40]=[C:41]=[O:42])([CH3:39])[CH3:38].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[NH2:3][C:4]1[C:13]2[N:14]=[C:15]([CH2:22][O:23][CH2:24][CH3:25])[N:16]([CH2:17][C:18]([OH:20])([CH3:21])[CH3:19])[C:12]=2[C:11]2[CH:10]=[CH:9][C:8]([O:26][CH2:27][CH2:28][NH:29][C:41]([NH:40][CH:37]([CH3:39])[CH3:38])=[O:42])=[CH:7][C:6]=2[N:5]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 61277Isopropyl isocyanateHCID 68972619HCID 68972619, compound

Product 1

HCID 58833647HCID 58833647, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[4-Amino-7-(2-aminoethoxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol dihydrochloride (prepared as described in Part A of Example 654, 0.466 g, 1.00 mmol), dichloromethane (10 mL), and triethylamine (0.418 mL, 3.0 mmol) were combined. The mixture was stirred for 10 minutes. Isopropyl isocyanate (0.097 mL, 1.00 mmol) was added and the reaction was stirred for 16 hours. Saturated aqueous sodium carbonate (˜8 mL) was added and the layers were separated. The organic layer was concentrated and purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 2-25% CMA in chloroform). The fractions containing product were combined and concentrated. Trituration of the product in dichloromethane, followed by filtration provided 0.319 g of N-(2-{[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethyl)-N′-isopropylurea as an off-white powder.

Workup

  1. stirringthe reaction was stirred for 16 hours
  2. customthe layers were separated
  3. concentrationThe organic layer was concentrated
  4. custompurified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 2-25% CMA in chloroform)
  5. additionThe fractions containing product
  6. concentrationconcentrated
  7. filtrationTrituration of the product in dichloromethane, followed by filtration

Sources & evidence

ORD record
ord-1fbb8cd692c9475687b7ebb81fd7d7ea
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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