Acetic Acid → HCID 59130454, compound

HRID 1992616Notes

Reaction equation

HRID 1992616 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:23][O:24][CH2:25][CH3:26])[N:14]([CH2:15][CH2:16][CH2:17][O:18][N:19]=[C:20]([CH3:22])[CH3:21])[C:10]=2[C:9]2[N:8]=[CH:7][C:6]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:5][C:4]=2[N:3]=1.C([BH3-])#N.[Na+].O1CCCC1.C(O)(=O)C>CO>[CH2:25]([O:24][CH2:23][C:13]1[N:14]([CH2:15][CH2:16][CH2:17][O:18][NH:19][CH:20]([CH3:21])[CH3:22])[C:10]2[C:9]3[N:8]=[CH:7][C:6]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=1)[CH3:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 58835261HCID 58835261, compound

Product 1

HCID 59130454HCID 59130454, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A slurry of acetone O-{3-[4-amino-2-(ethoxymethyl)-7-phenyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]propyl}oxime (1.00 g, 2.31 mmol), 1 M sodium cyanoborohydride in tetrahydrofuran (4.62 mL, 4.62 mmol), methanol (12 mL), and acetic acid (4.5 mL) was stirred overnight at ambient temperature. The resulting solution was concentrated under reduced pressure and the residue was dissolved in chloroform (200 mL). The solution was washed with saturated aqueous sodium bicarbonate (2×40 mL) and brine (30 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 1.0 g of 2-(ethoxymethyl)-1-{3-[(isopropylamino)oxy]propyl}-7-phenyl-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine as a yellow powder, mp 142.0-144.0° C.

Workup

  1. concentrationThe resulting solution was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in chloroform (200 mL)
  3. washThe solution was washed with saturated aqueous sodium bicarbonate (2×40 mL) and brine (30 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-977271b900f64bed99cc8a087d47d55f
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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