Isobutyryl chloride → N-(2-{[4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl]oxy}ethyl)-2-methylpropanamide hydrochloride

HRID 540819Notes

Reaction equation

HRID 540819 reaction equation
[C:1]([Cl:6])(=[O:5])[CH:2]([CH3:4])[CH3:3].[NH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:20]=[CH:19][C:18]2[N:17]=[C:16]([NH2:21])[C:15]3[N:22]=[C:23]([CH2:28][O:29][CH2:30][CH3:31])[N:24]([CH2:25][CH2:26][CH3:27])[C:14]=3[C:13]=2[CH:12]=1>ClCCl>[ClH:6].[NH2:21][C:16]1[C:15]2[N:22]=[C:23]([CH2:28][O:29][CH2:30][CH3:31])[N:24]([CH2:25][CH2:26][CH3:27])[C:14]=2[C:13]2[CH:12]=[C:11]([O:10][CH2:9][CH2:8][NH:7][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[CH:20]=[CH:19][C:18]=2[N:17]=1

Participants

4

Reactant 2

HCID 62325Isobutyryl chlorideHCID 588336918-(2-aminoethoxy)-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 68970600N-(2-{[4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl]oxy}ethyl)-2-methylpropanamide hydrochlorideYield 77.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Isobutyryl chloride (0.160 mL, 1.53 mmol) was added dropwise to a solution of 8-(2-aminoethoxy)-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine (0.500 g, 1.46 mmol) in dichloromethane (10 mL), and the reaction was stirred for 16 hours. A precipitate formed, and dichloromethane (10 mL) was added. The precipitate was isolated by filtration, washed with dichloromethane (20 mL) and diethyl ether (75 mL), and dried for one hour under reduced pressure to provide 0.511 g of N-(2-{[4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl]oxy}ethyl)-2-methylpropanamide hydrochloride as an off-white solid, mp 240-242° C.

Workup

  1. customA precipitate formed
  2. customThe precipitate was isolated by filtration
  3. washwashed with dichloromethane (20 mL) and diethyl ether (75 mL)
  4. customdried for one hour under reduced pressure

Sources & evidence

ORD record
ord-d1dce1c5a4ad4cc7b37685f16e102a4a
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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