Sodium Hydroxide → HCID 57455390, compound

HRID 1623101Notes

Reaction equation

HRID 1623101 reaction equation
[OH-].[Na+].[CH2:3]([C:7]1[N:8]([CH2:20][CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])[C:9]2[C:18]3[N:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:19]=1)[CH2:4][CH2:5][CH3:6]>C(O)C>[CH2:3]([C:7]1[N:8]([CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:9]2[C:18]3[N:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:19]=1)[CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57455389HCID 57455389, compound

Product 1

HCID 57455390HCID 57455390, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aqueous sodium hydroxide (6M, 4 mL, 24 mmol, 2 eq) was added to a solution of ethyl 4-(2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyrate (4.1 g, 12.0 mmol, 1.0 eq) in ethanol (50 mL) and stirred overnight at ambient temperature. The reaction mixture was concentrated under reduced pressure, dissolved in water (15 mL) and adjusted to a pH of 4. The precipitate was filtered and dried at 65° C. under vacuum to afford 3.53 g of 4-(2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyric acid as a tan powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in water (15 mL)
  3. filtrationThe precipitate was filtered
  4. customdried at 65° C. under vacuum

Sources & evidence

ORD record
ord-7b2fb3dd250d457786321ff37f28c70b
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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