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

HRID 2366684Notes

Reaction equation

HRID 2366684 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[N:12]1([C:18](=[O:39])[CH2:19][CH2:20][CH2:21][CH2:22][N:23]2[C:35]3[C:34]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[N:28]=[CH:27][C:26]=3[N:25]=[C:24]2[CH2:36][CH2:37][CH3:38])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.[OH-].[NH4+:41].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[N:12]1([C:18](=[O:39])[CH2:19][CH2:20][CH2:21][CH2:22][N:23]2[C:35]3[C:34]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[N:28]=[C:27]([NH2:41])[C:26]=3[N:25]=[C:24]2[CH2:36][CH2:37][CH3:38])[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 695067201-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-1H-imidazo[4,5-c]quinoline

Product 1

HCID 574470661-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

mCPBA (6.56 g, 28.5 mmol) was added to a solution of 1-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-1H-imidazo[4,5-c]quinoline (6.2 g, 16 mmol) in chloroform (100 mL); the reaction was stirred for three hours at ambient temperature. Ammonium hydroxide (50 mL) was added. p-Toluenesulfonyl chloride (6.056 g, 31.76 mmol) was added over a period of five minutes, and the reaction was stirred for one hour. The work-up procedure and chromatographic purification was carried out as described in Part D of Example 8. The resulting oil was triturated with acetone, isolated by filtration, and dried to provide 1-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine as a tan powder, mp 178-179° C.

Workup

  1. stirringthe reaction was stirred for one hour
  2. customThe work-up procedure and chromatographic purification
  3. customThe resulting oil was triturated with acetone
  4. customisolated by filtration
  5. customdried

Sources & evidence

ORD record
ord-fd9b090e85fc414f8765089829f6674c
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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