4-Toluenesulfonyl chloride → HCID 57447119, compound

HRID 2366733Notes

Reaction equation

HRID 2366733 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[CH2:12]([O:14][CH2:15][C:16]1[N:17]([CH2:29][C:30]2([C:33]([NH2:35])=[O:34])[CH2:32][CH2:31]2)[C:18]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][C:19]=2[N:28]=1)[CH3:13].[OH-].[NH4+:37].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[NH2:37][C:20]1[C:19]2[N:28]=[C:16]([CH2:15][O:14][CH2:12][CH3:13])[N:17]([CH2:29][C:30]3([C:33]([NH2:35])=[O:34])[CH2:32][CH2:31]3)[C:18]=2[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N:21]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69506737HCID 69506737, compound

Product 1

HCID 57447119HCID 57447119, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

mCPBA (1.68 g, 6.81 mmol) was added to a suspension of 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclopropanecarboxamide (1.70 g, 5.24 mmol) in chloroform (25 mL); the reaction was stirred for two hours at ambient temperature and then cooled to 0° C. Ammonium hydroxide (5 mL) and p-toluenesulfonyl chloride (1.10 g, 5.76 mmol) were added. The reaction was stirred for one hour at 5° C. and then filtered to isolate a precipitate. The precipitate was triturated with 2 M aqueous sodium hydroxide, isolated by filtration, triturated with hot acetonitrile, isolated by filtration, and recrystallized from ethanol. The crystals were dried overnight at 85° C. in a vacuum oven to provide 0.78 g of 1-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclopropanecarboxamide as tan needles, mp 230.5-232.5° C.

Workup

  1. temperaturecooled to 0° C
  2. stirringThe reaction was stirred for one hour at 5° C.
  3. filtrationfiltered
  4. customto isolate a precipitate
  5. customThe precipitate was triturated with 2 M aqueous sodium hydroxide
  6. customisolated by filtration
  7. customtriturated with hot acetonitrile
  8. customisolated by filtration
  9. customrecrystallized from ethanol
  10. customThe crystals were dried overnight at 85° C. in a vacuum oven

Sources & evidence

ORD record
ord-98d74e4863cd42b3aecf613506b19b3b
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

Loading…