Acetyl chloride → HCID 58833667, compound

HRID 540862Notes

Reaction equation

HRID 540862 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-7c110cda576d47edb791e6ca9bb70dfb
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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