Water → HCID 58833705, compound

HRID 540893Notes

Reaction equation

HRID 540893 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[CH3:7][O:8][CH2:9][CH2:10][C:11]1[N:12]([CH2:32][CH2:33][CH3:34])[C:13]2[C:22]3[CH:21]=[CH:20][C:19]([O:23][CH:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)=[CH:18][C:17]=3[N:16]=[C:15]([NH2:30])[C:14]=2[N:31]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(Cl)(Cl)Cl>[C:1]([N:27]1[CH2:26][CH2:25][CH:24]([O:23][C:19]2[CH:20]=[CH:21][C:22]3[C:13]4[N:12]([CH2:32][CH2:33][CH3:34])[C:11]([CH2:10][CH2:9][O:8][CH3:7])=[N:31][C:14]=4[C:15]([NH2:30])=[N:16][C:17]=3[CH:18]=2)[CH2:29][CH2:28]1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 62325Isobutyryl chlorideHCID 68972633HCID 68972633, compound

Product 1

HCID 58833705HCID 58833705, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Isobutyryl chloride (0.273 mL, 2.61 mmol) was added dropwise to a stirred solution of 2-(2-methoxyethyl)-7-(piperidin-4-yloxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-ylamine (prepared as described in Part A of Example 388, 1.00 g, 2.61 mmol) in chloroform at 0° C. After 2 hours, the solution was allowed to warm to ambient temperature for 1 hour. Saturated aqueous sodium carbonate (15 mL) and water (10 mL) were added and the mixture was allowed to stir for 16 hours. The mixture was transferred to a separatory funnel, the layers were separated, and the aqueous layer was extracted with dichloromethane (2×30 mL). The organic layers were combined, washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. Recrystallization from acetonitrile afforded 1.00 g of 7-[(1-isobutyrylpiperidin-4-yl)oxy]-2-(2-methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine as a flocculent white solid, mp 165-166° C.

Workup

  1. customprepared
  2. customat 0° C
  3. customThe mixture was transferred to a separatory funnel
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with dichloromethane (2×30 mL)
  6. washwashed with water and saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-eb736c9ca3e84204af1acf0df12eba3c
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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