Benzenesulfonyl chloride → 2-(2-methoxyethyl)-1-(5-morpholin-4-yl-5-oxopentyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 2366690Notes

Reaction equation

HRID 2366690 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:12][O:13][CH2:14][CH2:15][C:16]1[N:17]([CH2:29][CH2:30][CH2:31][CH2:32][C:33]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)=[O:34])[C:18]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][C:19]=2[N:28]=1.[OH-].[NH4+:42].C1(S(Cl)(=O)=O)C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:12][O:13][CH2:14][CH2:15][C:16]1[N:17]([CH2:29][CH2:30][CH2:31][CH2:32][C:33]([N:35]2[CH2:36][CH2:37][O:38][CH2:39][CH2:40]2)=[O:34])[C:18]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[C:20]([NH2:42])[C:19]=2[N:28]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 695066852-(2-methoxyethyl)-1-(5-morpholin-4-yl-5-oxopentyl)-1H-imidazo[4,5-c]quinoline

Product 1

HCID 589703762-(2-methoxyethyl)-1-(5-morpholin-4-yl-5-oxopentyl)-1H-imidazo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

mCPBA (6.60 g, 28.7 mmol) was added to a solution of 2-(2-methoxyethyl)-1-(5-morpholin-4-yl-5-oxopentyl)-1H-imidazo[4,5-c]quinoline (6.5 g, 17 mmol) in chloroform (100 mL); the reaction was stirred for two hours at ambient temperature. The reaction was cooled to 0° C., and ammonium hydroxide (50 mL) was added. A solution of benzenesulfonyl chloride (4.11 mL, 33.0 mmol) in chloroform (20 mL) was added over a period of 20 minutes, and the reaction was allowed to warm to ambient temperature and stirred for two hours. The work-up procedure and chromatographic purification was carried out as described in Part D of Example 8. The resulting product was triturated with 10% aqueous sodium hydroxide, isolated by filtration, washed with water, and dried overnight in a vacuum oven to provide 2-(2-methoxyethyl)-1-(5-morpholin-4-yl-5-oxopentyl)-1H-imidazo[4,5-c]quinolin-4-amine as an off-white powder, mp 128-129° C.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. temperatureto warm to ambient temperature
  3. stirringstirred for two hours
  4. customThe work-up procedure and chromatographic purification
  5. customThe resulting product was triturated with 10% aqueous sodium hydroxide
  6. customisolated by filtration
  7. washwashed with water
  8. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-308a0c783613483285b7544af4682e31
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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