4-Toluenesulfonyl chloride → HCID 58970372, compound

HRID 2366665Notes

Reaction equation

HRID 2366665 reaction equation
[CH3:1][C:2]([CH3:23])([CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:9]=[C:8]1[CH2:20][CH2:21][CH3:22])[C:3]([NH2:5])=[O:4].C1C=C(Cl)C=C(C(OO)=O)C=1.[OH-].[NH4+:36].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>>[NH2:36][C:11]1[C:10]2[N:9]=[C:8]([CH2:20][CH2:21][CH3:22])[N:7]([CH2:6][C:2]([CH3:23])([CH3:1])[C:3]([NH2:5])=[O:4])[C:19]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acid2×HCID 57447058HCID 57447058, compound

Product 1

HCID 58970372HCID 58970372, compound

Conditions

Temperature
0 °C

Procedure

2,2-Dimethyl-3-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propanamide was treated with mCPBA (3.24 g, 14.4 mmol) followed by ammonium hydroxide (75 mL) and p-toluenesulfonyl chloride (2.5 g, 13 mmol) according to a modification of the method described in Part F of Example 1. The reaction was cooled to 0° C. before the addition of mCPBA. After the addition, the reaction was stirred for 15 minutes at 0° C. and 1.75 hours at ambient temperature. The reaction was not washed prior to the addition of ammonium hydroxide. The amination reaction was stirred for one hour. The crude product was purified by column chromatography on silica gel (eluting with 90:10 dichloromethane:methanol), recrystallized from toluene:methanol, dried overnight in a vacuum oven at 80° C., recrystallized from acetonitrile:water, and dried overnight in a vacuum oven at 80° C. to provide 0.553 g of 3-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanamide as a yellow solid, mp 219-221° C.

Workup

  1. additionAfter the addition
  2. washThe reaction was not washed
  3. additionto the addition of ammonium hydroxide
  4. customThe amination reaction
  5. stirringwas stirred for one hour
  6. customThe crude product was purified by column chromatography on silica gel (eluting with 90:10 dichloromethane:methanol)
  7. customrecrystallized from toluene
  8. dry with materialmethanol, dried overnight in a vacuum oven at 80° C.
  9. customrecrystallized from acetonitrile
  10. dry with materialwater, and dried overnight in a vacuum oven at 80° C.

Sources & evidence

ORD record
ord-5d50df1443264736a578e1d051adc0f4
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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