4-Toluenesulfonyl chloride → HCID 57447048, compound

HRID 2366656Notes

Reaction equation

HRID 2366656 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][C:20]([NH2:22])=[O:21])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[Na+].C(=O)(O)[O-].[Na+].[OH-].[NH4+:53]>>[NH2:53][C:9]1[C:8]2[N:17]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[N:6]([CH2:18][CH2:19][C:20]([NH2:22])=[O:21])[C:7]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

7

Reactant 6

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 57447049HCID 57447049, compound

Product 1

HCID 57447048HCID 57447048, compound

Procedure

3-[2-(Ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propanamide (2.4 g, 8.1 mmol) was treated with mCPBA (3.24 g, 14.1 mmol) followed by ammonium hydroxide (40 mL) and p-toluenesulfonyl chloride (2.99 g, 15.7 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. After the amination reaction was stirred for two hours, 10% aqueous sodium hydroxide (25 mL) and saturated aqueous sodium bicarbonate (25 mL) were sequentially added with stirring. A precipitate formed and was isolated by filtration. The solid was triturated twice with 25% aqueous sodium hydroxide, isolated by filtration, washed with water, and dried in a vacuum oven for three days to provide 0.685 g of 3-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propanamide as tan needles, mp>250° C.

Workup

  1. washThe reaction was not washed with 10% aqueous sodium hydroxide
  2. additionto the addition of ammonium hydroxide
  3. customAfter the amination reaction
  4. stirringwith stirring
  5. customA precipitate formed
  6. customwas isolated by filtration
  7. customThe solid was triturated twice with 25% aqueous sodium hydroxide
  8. customisolated by filtration
  9. washwashed with water
  10. customdried in a vacuum oven for three days

Sources & evidence

ORD record
ord-f6a9a51822e64e67b693f4fac58da92d
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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