Acetyl chloride → HCID 58833667, compound

HRID 2203539Notes

Reaction equation

HRID 2203539 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:23][O:24][CH2:25][CH3:26])[N:14]([CH2:15][C:16]([NH:19][C:20](=[O:22])[CH3:21])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][NH2:34])=[CH:5][C:4]=2[N:3]=1.[C:35](Cl)(=[O:37])[CH3:36].CS(OS(C)(=O)=O)(=O)=O>>[C:35]([NH:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][O:27][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[N:14]([CH2:15][C:16]([NH:19][C:20](=[O:22])[CH3:21])([CH3:18])[CH3:17])[C:13]([CH2:23][O:24][CH2:25][CH3:26])=[N:12][C:11]=3[C:2]([NH2:1])=[N:3][C:4]=2[CH:5]=1)(=[O:37])[CH3:36]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 81560Methanesulfonic anhydrideHCID 68972044HCID 68972044, compound

Product 1

HCID 58833667HCID 58833667, compoundYield 36.7%

Procedure

A modification of the method described in Part K of Example 45 was followed using N-{2-[4-amino-7-(6-aminohexyloxy)-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}acetamide (1.2 g, 2.5 mmol) as the starting material and acetyl chloride (200 μL, 3 mmol) in lieu of methanesulfonic anhydride. Following chromatographic purification, the solid was recrystallized from acetonitrile, and the crystals were dissolved in dichloromethane:methanol, concentrated under reduced pressure, and further dried under high vacuum at 60° C. to provide 0.47 g of N-(2-{7-[6-(acetylamino)hexyloxy]-4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl}-1,1-dimethylethyl)acetamide as a white powder, mp 190-192° C.

Workup

  1. custompurification
  2. customthe solid was recrystallized from acetonitrile
  3. dissolutionthe crystals were dissolved in dichloromethane
  4. concentrationmethanol, concentrated under reduced pressure
  5. customfurther dried under high vacuum at 60° C.

Sources & evidence

ORD record
ord-24fd880e6c7c4ca4ba16f2b5637844bd
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

Loading…