Hydrochloric Acid → HCID 11673659, compound

HRID 81899Notes

Reaction equation

HRID 81899 reaction equation
B(Br)(Br)Br.Br.[NH2:6][C:7]1[C:16]2[N:17]=[C:18]([CH2:25][O:26]CC)[N:19]([CH2:20][C:21]([CH3:24])([OH:23])[CH3:22])[C:15]=2[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]=1.Cl.[OH-].[Na+]>ClCCl.CO>[NH2:6][C:7]1[C:16]2[N:17]=[C:18]([CH2:25][OH:26])[N:19]([CH2:20][C:21]([CH3:22])([OH:23])[CH3:24])[C:15]=2[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 68930462HCID 68930462, compound

Product 1

HCID 11673659HCID 11673659, compoundYield 48.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide in dichloromethane (11.8 mL of 1 M) was added to a chilled (0° C.) suspension of 1-(4-amino-2-ethoxymethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol hydrobromide (1.24 g, 3.93 mmol) in dichloromethane (30 mL). The reaction mixture was allowed to come to ambient temperature with stirring for 16 hours. Methanol (15 mL) and hydrochloric acid (10 mL of 6 N) were added and the reaction mixture was heated at reflux for 2.5 hours. The reaction mixture was made basic with sodium hydroxide and the layers were separated. The aqueous layer was extracted with ethyl acetate (3×100 mL). The combined extracts were washed sequentially with water and brine, dried over magnesium sulfate, and then concentrated under reduced pressure to provide a white solid. This material was crystallized from ethyl acetate and then dried under vacuum at 95° C. for 16 hours to provide 0.55 g of 1-(4-amino-2-hydroxymethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol as a white powder, mp 235-237° C. Anal. calcd for C14H17N5O2: % C, 58.52; % H, 5.96; % N, 24.37. Found: % C, 58.40; % H, 5.82; % N, 24.45.

Workup

  1. temperaturea chilled
  2. customto come to ambient temperature
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 2.5 hours
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
  7. washThe combined extracts were washed sequentially with water and brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customto provide a white solid
  11. customThis material was crystallized from ethyl acetate
  12. customdried under vacuum at 95° C. for 16 hours

Sources & evidence

ORD record
ord-5dfc4b2c2df54de2a626c31c4f9aa302
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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