4-Toluenesulfonyl chloride → 5-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanamide

HRID 2366686Notes

Reaction equation

HRID 2366686 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([NH2:23])=[O:22])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].C1C=C(Cl)C=C(C(OO)=O)C=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:47]>>[NH2:47][C:8]1[C:7]2[N:16]=[C:4]([CH2:1][CH2:2][CH3:3])[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([NH2:23])=[O:22])[C:6]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 574470715-(2-Propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanamide

Product 1

HCID 589703695-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanamide

Procedure

5-(2-Propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanamide (4.4 g, 14 mmol) was treated with mCPBA (4.28 g, 24.8 mmol), ammonium hydroxide (40 mL), and p-toluenesulfonyl chloride (5.24 g, 27.4 mmol) according to a modification of the method described in Part F of Example 34. At the completion of the amination reaction, a precipitate was present and was isolated by filtration. The precipitate was triturated and sonicated with acetone, isolated by filtration, and dried in a vacuum oven at 80° C. to provide 1.28 g of 5-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanamide as a tan powder, mp 202-203° C.

Workup

  1. customAt the completion of the amination reaction
  2. customwas isolated by filtration
  3. customThe precipitate was triturated
  4. customsonicated with acetone
  5. customisolated by filtration
  6. customdried in a vacuum oven at 80° C.

Sources & evidence

ORD record
ord-d1935c81d0ed40e5a5481b36f40dee59
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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