Cesium carbonate → tert-butyl 2-{[1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethylcarbamate

HRID 540885Notes

Reaction equation

HRID 540885 reaction equation
[CH3:1][C:2]1([CH3:26])[O:6][CH:5]([CH2:7][N:8]2[C:20]3[C:19]4[CH:18]=[CH:17][C:16]([OH:21])=[CH:15][C:14]=4[N:13]=[CH:12][C:11]=3[N:10]=[C:9]2[CH2:22][O:23][CH2:24][CH3:25])[CH2:4][O:3]1.I[CH2:28][CH2:29][NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:1][C:2]1([CH3:26])[O:6][CH:5]([CH2:7][N:8]2[C:20]3[C:19]4[CH:18]=[CH:17][C:16]([O:21][CH2:28][CH2:29][NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:15][C:14]=4[N:13]=[CH:12][C:11]=3[N:10]=[C:9]2[CH2:22][O:23][CH2:24][CH3:25])[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 641024tert-butyl N-(2-iodoethyl)carbamateHCID 1363478501-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-ol

Product 1

HCID 68972116tert-butyl 2-{[1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethylcarbamateYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using a modification on the procedure described in Part L of Example 2, 1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-ol (8.50 g, 23.8 mmol) was treated with tert-butyl 2-iodoethylcarbamate (7.10 g, 26.2 mmol) and cesium carbonate (11.62 g, 35.67 mmol) in DMF (120 mL). During the workup, after the reaction mixture was concentrated under reduced pressure, the residue was treated with water (75 mL) and stirred for 30 minutes. A precipitate was isolated by filtration and washed with diethyl ether to yield 8.7 g of tert-butyl 2-{[1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethylcarbamate as an off-white solid, mp 152-153° C.

Workup

  1. concentrationDuring the workup, after the reaction mixture was concentrated under reduced pressure
  2. additionthe residue was treated with water (75 mL)
  3. customA precipitate was isolated by filtration
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-56456dc3bfa04d0ea842cbd0adab414d
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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