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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 2203561
Notes
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Reaction equation

HRID 2203561 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent

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-6bd45e34b9d24a5b9d7cc4178be71663
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09365567B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes