Sodium Chloride → HCID 58833648, compound

HRID 2203631Notes

Reaction equation

HRID 2203631 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:20]([CH2:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[C:19]([CH2:28][CH3:29])=[N:18][C:12]=3[C:13]([NH2:17])=[N:14][C:15]=2[CH:16]=1.[Cl-].[Na+].[OH-].[Na+]>O>[NH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:20]([CH2:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[C:19]([CH2:28][CH3:29])=[N:18][C:12]=3[C:13]([NH2:17])=[N:14][C:15]=2[CH:16]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 68971491HCID 68971491, compound

Product 1

HCID 58833648HCID 58833648, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7-(2-Aminoethoxy)-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochloride (prepared as described in Example 552, 0.100 g) was dissolved in water (5 mL) and saturated aqueous sodium chloride (5 mL). The solution was brought to pH 13 with 50% aqueous sodium hydroxide and extracted with chloroform. The chloroform was washed successively with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was recrystallized from acetonitrile to provide 0.065 g of 7-(2-aminoethoxy)-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a white crystalline solid, mp 238° C. (decomposition).

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform was washed successively with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-fe6eabc49d2c4c6393494f0b2fd653ef
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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