Sodium Carbonate → HCID 58833673, compound

HRID 540916Notes

Reaction equation

HRID 540916 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=O)=[O:3].[CH2:10]([O:12][CH2:13][C:14]1[N:15]([CH2:35][CH2:36][CH3:37])[C:16]2[C:25]3[CH:24]=[C:23]([O:26][CH:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)[CH:22]=[CH:21][C:20]=3[N:19]=[C:18]([NH2:33])[C:17]=2[N:34]=1)[CH3:11].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH2:10]([O:12][CH2:13][C:14]1[N:15]([CH2:35][CH2:36][CH3:37])[C:16]2[C:25]3[CH:24]=[C:23]([O:26][CH:27]4[CH2:28][CH2:29][N:30]([S:2]([CH3:1])(=[O:5])=[O:3])[CH2:31][CH2:32]4)[CH:22]=[CH:21][C:20]=3[N:19]=[C:18]([NH2:33])[C:17]=2[N:34]=1)[CH3:11]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 81560Methanesulfonic anhydrideHCID 58833720HCID 58833720, compound

Product 1

HCID 58833673HCID 58833673, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic anhydride (0.295 g, 1.69 mmol) was added in one portion to a stirred solution of 2-(ethoxymethyl)-8-(piperidin-4-yloxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine (prepared as described in Example 411, 0.650 g, 1.69 mmol) in dichloromethane (15 mL) at room temperature, resulting in a white precipitate. After 16 hours, 2.0 M aqueous sodium carbonate was added and the reaction mixture was allowed to stir for 45 minutes. The precipitate dissolved and the mixture was transferred to a separatory funnel where the layers were separated. The aqueous layer was extracted with chloroform. The organic layers were combined, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by trituration in boiling acetonitrile and isolated by filtration to yield 0.650 g of 2-(ethoxymethyl)-8-{[1-(methylsulfonyl)piperidin-4-yl]oxy}-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine as an off-white crystalline solid, mp 240-243.5° C.

Workup

  1. customresulting in a white precipitate
  2. dissolutionThe precipitate dissolved
  3. customthe mixture was transferred to a separatory funnel
  4. customwhere the layers were separated
  5. extractionThe aqueous layer was extracted with chloroform
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified by trituration
  11. customisolated by filtration

Sources & evidence

ORD record
ord-58bf924a4a444b9cb793448f4d8942c4
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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