Acetyl chloride → HCID 15984032, compound

HRID 445101Notes

Reaction equation

HRID 445101 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:28][O:29][CH2:30][CH3:31])[N:18]([CH2:19][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])([CH3:22])[CH3:21])[C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1.C(N(CC)CC)C.C(OC(=O)C)(=O)C>CN(C)C=O>[CH2:30]([O:29][CH2:28][C:17]1[N:18]([CH2:19][C:20]([CH3:22])([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH3:21])[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([NH:5][C:1](=[O:3])[CH3:2])[C:15]=2[N:16]=1)[CH3:31]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 9843452HCID 9843452, compound

Product 1

HCID 15984032HCID 15984032, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Acetyl chloride (150 μL, 1.1 equivalents (eq)) was added to N-{2-[4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide (750 mg, 1 eq) in a mixture of triethylamine (401 μL, 1.5 eq) and N,N-dimethylformamide (DMF) (5 mL) and the resulting solution was stirred at ambient temperature. After 2 hours acetic anhydride (1 mL) was added. The reaction mixture was stirred at ambient temperature for 1 hour and then concentrated under reduced pressure. The residue was purified by automated flash chromatography (silica gel eluted with a gradient of 0-10% methanol in dichloromethane containing 1% ammonium hydroxide) to provide 278 mg of N-(2-ethoxymethyl-1-{2-methyl-2-[(methylsulfonyl)amino]propyl}-1H-imidazo[4,5-c]quinolin-4-yl)acetamide as a white powder, mp 75-76° C. Anal. calcd for C20H27N5O4S.0.40H2O: C, 54.50; H, 6.36; N, 15.89. Found: C, 54.70; H, 6.10; N, 15.58.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 1 hour
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by automated flash chromatography (silica gel
  4. washeluted with a gradient of 0-10% methanol in dichloromethane containing 1% ammonium hydroxide)

Sources & evidence

ORD record
ord-37388f1a6e7545038ee03737ae5dcd9c
Source dataset
uspto-grants-2013_07
Patent number
US08476292B2

Reaction notes

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