4-Toluenesulfonyl chloride → HCID 57447064, compound

HRID 2366676Notes

Reaction equation

HRID 2366676 reaction equation
[CH3:1][C:2]1[N:3]([CH2:15][CH2:16][C:17]([NH:19][CH2:20][CH2:21][CH3:22])=[O:18])[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:14]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:46]>>[NH2:46][C:6]1[C:5]2[N:14]=[C:2]([CH3:1])[N:3]([CH2:15][CH2:16][C:17]([NH:19][CH2:20][CH2:21][CH3:22])=[O:18])[C:4]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69506707HCID 69506707, compound

Product 1

HCID 57447064HCID 57447064, compound

Procedure

3-(2-Methyl-1H-imidazo[4,5-c]quinolin-1-yl)-N-propylpropanamide (610 g, 20.2 mmol) was treated with mCPBA (8.15 g, 35.4 mmol) followed by ammonium hydroxide (40 mL) and p-toluenesulfonyl chloride (7.52 g, 39.5 mmol) according to a modification of the method described in Part D of Example 8. The reaction was not washed with 10% aqueous sodium hydroxide prior to the addition of ammonium hydroxide. The crude product was twice triturated with ethyl acetate and isolated by filtration. The solid was then purified by column chromatography on silica gel (eluting with 90:10 dichloromethane:methanol). The product was then triturated sequentially with 10% aqueous sodium hydroxide and acetone (2×). The solid was then purified again by column chromatography on silica gel (eluting with dichloromethane:methanol in a gradient from 95:5 to 90:10). The resulting solid was triturated with 10% aqueous sodium hydroxide, isolated by filtration, washed with water, and dried overnight to provide 0.477 g of 3-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)-N-propylpropanamide as an off-white powder, mp 188-189° C.

Workup

  1. washThe reaction was not washed with 10% aqueous sodium hydroxide
  2. additionto the addition of ammonium hydroxide
  3. customThe crude product was twice triturated with ethyl acetate
  4. customisolated by filtration
  5. customThe solid was then purified by column chromatography on silica gel (eluting with 90:10 dichloromethane:methanol)
  6. customThe product was then triturated sequentially with 10% aqueous sodium hydroxide and acetone (2×)
  7. customThe solid was then purified again by column chromatography on silica gel (
  8. washeluting with dichloromethane
  9. customThe resulting solid was triturated with 10% aqueous sodium hydroxide
  10. customisolated by filtration
  11. washwashed with water
  12. customdried overnight

Sources & evidence

ORD record
ord-2fdac9a234764d648d000692b74ac63d
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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