Acetic Anhydride → HCID 58833645, compound

HRID 540939Notes

Reaction equation

HRID 540939 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:26][CH2:27][CH3:28])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([O:17][CH:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)=[CH:12][C:11]=3[N:10]=[C:9]([NH2:24])[C:8]=2[N:25]=1)[CH3:2].[C:29](OC(=O)C)(=[O:31])[CH3:30].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[C:29]([N:21]1[CH2:20][CH2:19][CH:18]([O:17][C:13]2[CH:14]=[CH:15][C:16]3[C:7]4[N:6]([CH2:26][CH2:27][CH3:28])[C:5]([CH2:4][O:3][CH2:1][CH3:2])=[N:25][C:8]=4[C:9]([NH2:24])=[N:10][C:11]=3[CH:12]=2)[CH2:23][CH2:22]1)(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 58833655HCID 58833655, compound

Product 1

HCID 58833645HCID 58833645, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(Ethoxymethyl)-7-(piperidin-4-yloxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine (0.500 g, 1.3 mmol) was slurried in dichloromethane (13 mL). Acetic anhydride (0.122 mL, 1.3 mmol) was added dropwise to the slurry and the mixture was stirred for 36 hours. Saturated aqueous sodium carbonate (5 mL) was added and the reaction was stirred for 1 hour. The layers were separated and the organic fraction was purified by chromatography on a HORIZON BPFC system (silica gel, gradient elution with 1-22% CMA in chloroform). The resulting amorphous solid was triturated with boiling acetonitrile. Filtration afforded 0.270 g of 7-[(1-acetylpiperidin-4-yl)oxy]-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine as an off-white solid, mp 178-179.5° C.

Workup

  1. stirringthe reaction was stirred for 1 hour
  2. customThe layers were separated
  3. customthe organic fraction was purified by chromatography on a HORIZON BPFC system (silica gel, gradient elution with 1-22% CMA in chloroform)
  4. customThe resulting amorphous solid was triturated with boiling acetonitrile
  5. filtrationFiltration

Sources & evidence

ORD record
ord-81537404aabc4cd687235045bc1d640f
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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