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4-Toluenesulfonyl chloride → tert-butyl 2-[(4-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate

HRID 2203493
Notes
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Reaction equation

HRID 2203493 reaction equation
[OH-].[NH4+:2].[CH2:3]([O:5][CH2:6][C:7]1[N:8]([CH2:32][CH2:33][CH3:34])[C:9]2[C:18]3[CH:17]=[C:16]([O:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:15]=[CH:14][C:13]=3[N+:12]([O-])=[CH:11][C:10]=2[N:31]=1)[CH3:4].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[C:25]([O:24][C:23](=[O:29])[NH:22][CH2:21][CH2:20][O:19][C:16]1[CH:15]=[CH:14][C:13]2[N:12]=[C:11]([NH2:2])[C:10]3[N:31]=[C:7]([CH2:6][O:5][CH2:3][CH3:4])[N:8]([CH2:32][CH2:33][CH3:34])[C:9]=3[C:18]=2[CH:17]=1)([CH3:28])([CH3:27])[CH3:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 68973926tert-butyl 2-[(2-ethoxymethyl-5-oxido-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate

Product 1

HCID 68974513tert-butyl 2-[(4-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

Ammonium hydroxide (50 mL) was added to a solution of tert-butyl 2-[(2-ethoxymethyl-5-oxido-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate (9.7 g, 22 mmol) in dichloromethane (120 mL), and the mixture was cooled to 10° C. p-Toluenesulfonyl chloride (4.16 g, 21.8 mmol) was added in small portions, while maintaining the reaction temperature below 15° C. The reaction was stirred for 16 hours; a tan precipitate formed. Dichloromethane (500 mL) was added, and the precipitate was isolated by filtration and washed with diethyl ether to provide 3.98 g of tert-butyl[2-(4-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yloxy)ethyl]carbamate as a fine powder. The organic layer was washed sequentially with ammonium hydroxide, water, and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was recrystallized from acetonitrile to provide 4.4 g of tert-butyl 2-[(4-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate as a peach-colored powder.

Workup

  1. additionwas added in small portions
  2. temperaturewhile maintaining the reaction temperature below 15° C
  3. customa tan precipitate formed
  4. customthe precipitate was isolated by filtration
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-c40168ffce154ad6aa2461a560daf26f
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