Sodium Hydroxide → 3-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propan-1-ol

HRID 1992591Notes

Reaction equation

HRID 1992591 reaction equation
Cl.C([O:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][N:18]=2)[N:13]=[CH:12][C:11]=1[NH:20][C:21](=O)[CH2:22][CH2:23][CH3:24])(=O)C.[OH-].[Na+]>C(O)C>[CH2:22]([C:21]1[N:9]([CH2:8][CH2:7][CH2:6][OH:5])[C:10]2[C:19]3[N:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:20]=1)[CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68537702HCID 68537702, compound

Product 1

HCID 685386673-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To the 3-{[3-(butyrylamino)[1,5]naphthyridin-4-yl]amino}propyl acetate hydrochloride prepared in Part D was added ethanol (165 mL) and 2 M sodium hydroxide (62.0 mL, 124 mmol). The resulting solution was heated at 60° C. for 7 hours, and then was stirred at room temperature overnight. The solution was concentrated, and the resulting residue was dissolved in dichloromethane (250 mL) and washed with water (125 mL). The aqueous layer was extracted with dichloromethane (75 mL). The combined organic layers were washed with brine (100 mL), dried over magnesium sulfate, filtered, and concentrated to provide 9.24 g of 3-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propan-1-ol as a brown oil.

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe resulting residue was dissolved in dichloromethane (250 mL)
  3. washwashed with water (125 mL)
  4. extractionThe aqueous layer was extracted with dichloromethane (75 mL)
  5. washThe combined organic layers were washed with brine (100 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cba24fc4eeab4f8685879301d4f9731c
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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