4-Toluenesulfonyl chloride → HCID 58970368, compound

HRID 2366672Notes

Reaction equation

HRID 2366672 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:12][C:13]1[N:14]([CH2:26][CH2:27][C:28]([NH2:30])=[O:29])[C:15]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[CH:17][C:16]=2[N:25]=1.[OH-].[NH4+:32].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[NH2:32][C:17]1[C:16]2[N:25]=[C:13]([CH3:12])[N:14]([CH2:26][CH2:27][C:28]([NH2:30])=[O:29])[C:15]=2[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:18]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 57447063HCID 57447063, compound

Product 1

HCID 58970368HCID 58970368, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

mCPBA (3.48 g, 15.1 mmol) was added to a solution of 3-(2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)propanamide (2.20 g, 8.65 mmol) in chloroform (100 mL). The reaction was stirred for two hours at ambient temperature and cooled to 0° C. Ammonium hydroxide (40 mL) was added followed by p-toluenesulfonyl chloride (3.21 g, 16.9 mmol), which was added over a period of five minutes. The reaction was stirred for two hours at ambient temperature and then concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with dichloromethane:methanol in a gradient from 90:10 to 80:20). The resulting solid was triturated with 10% aqueous sodium hydroxide, isolated by filtration, washed with water, and dried overnight in a vacuum oven at 60° C. to provide 0.145 g of 3-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)propanamide as a off-white powder, mp 237-239° C.

Workup

  1. temperaturecooled to 0° C
  2. additionwas added over a period of five minutes
  3. stirringThe reaction was stirred for two hours at ambient temperature
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel (
  6. washeluting with dichloromethane
  7. customThe resulting solid was triturated with 10% aqueous sodium hydroxide
  8. customisolated by filtration
  9. washwashed with water
  10. customdried overnight in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-3c728408b3884b2090f8b7f7e8a01836
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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