Water → N-{2-[4-amino-2-(ethoxymethyl)-7-(prop-2-ynyloxy)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide

HRID 2383224Notes

Reaction equation

HRID 2383224 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:28][O:29][CH2:30][CH3:31])[N:18]([CH2:19][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])([CH3:22])[CH3:21])[C:14]=2[C:13]2[CH:12]=[CH:11][C:10]([OH:32])=[CH:9][C:8]=2[N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.ClCCl>[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:28][O:29][CH2:30][CH3:31])[N:18]([CH2:19][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])([CH3:22])[CH3:21])[C:14]=2[C:13]2[CH:12]=[CH:11][C:10]([O:32][CH2:3][C:2]#[CH:1])=[CH:9][C:8]=2[N:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 136075196N-[2-(4-amino-2-ethoxymethyl-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide

Product 1

HCID 86626178N-{2-[4-amino-2-(ethoxymethyl)-7-(prop-2-ynyloxy)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamideYield 24.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Propargyl bromide (1.30 g, 9.19 mmol) was added to a mixture of N-[2-(4-amino-2-ethoxymethyl-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide (2.5 g, 6.13 mmol) and cesium carbonate (5.00 g, 12.3 mmol) in DMF. The mixture was stirred overnight and then was poured into water (600 mL). The mixture was stirred overnight and a gummy solid was isolated by filtration. The solid was dissolved in dichloromethane and the resulting solution was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, gradient elution with 0-30% of a 1:5 methanol/dichloromethane solution in dichloromethane) to provide 675 mg of N-{2-[4-amino-2-(ethoxymethyl)-7-(prop-2-ynyloxy)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide as an off-white solid. A small portion was recrystallized from methanol to yield an off-white solid, mp 175.0-176.0° C.

Workup

  1. stirringThe mixture was stirred overnight
  2. customa gummy solid was isolated by filtration
  3. dry with materialthe resulting solution was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography (silica gel, gradient elution with 0-30% of a 1:5 methanol/dichloromethane solution in dichloromethane)

Sources & evidence

ORD record
ord-d5f56ef0e22a42d881037b8d98d800ab
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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