Hydrochloric Acid → HCID 57557270, compound

HRID 1798887Notes

Reaction equation

HRID 1798887 reaction equation
C([O:8][CH2:9][CH2:10][C:11]1[N:12]([CH2:25][C:26]([F:29])([CH3:28])[CH3:27])[C:13]2[C:22]3[N:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[C:15]([NH2:23])[C:14]=2[N:24]=1)C1C=CC=CC=1.Cl>CO.[Pd].C(O)C>[NH2:23][C:15]1[C:14]2[N:24]=[C:11]([CH2:10][CH2:9][OH:8])[N:12]([CH2:25][C:26]([F:29])([CH3:28])[CH3:27])[C:13]=2[C:22]2[N:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:16]=1

Participants

6

Reactant 2

HCID 313Hydrochloric Acid2×HCID 68930481HCID 68930481, compound

Product 1

HCID 57557270HCID 57557270, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent2×HCID 887MethanolSolvent

Procedure

A solution of 2-[2-(benzyloxy)ethyl]-1-(2-fluoro-2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine (0.78 g, 1.98 mmol) dissolved in 20 mL of methanol was treated with 10% palladium on carbon (200 mg) and 0.68 mL of 3 M HCl in ethanol. The mixture was shaken under H2 at 50 PSI (3.4×105 Pa) overnight. Additional 10% palladium on carbon (200 mg) and 3 M HCl in ethanol (0.33 mL) were added and shaking was continued for 24 hours. The reaction mixture was filtered through a pad of CELITE filter agent. The pad was rinsed with methanol and the combined filtrates were concentrated under reduced pressure. The resulting material was treated with 20 mL of H2O and 2 mL of concentrated NH4OH solution and extracted into CHCl3 (3×25 mL). The combined organic layers were concentrated under reduced pressure. Chromatography (SiO2, 15-30% CMA/CHCl3) gave a white powder. Crystallization from ethanol/H2O gave 276 mg of 2-[4-amino-1-(2-fluoro-2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]ethanol as white needles, mp 224-225° C.

Workup

  1. stirringshaking
  2. waitwas continued for 24 hours
  3. filtrationThe reaction mixture was filtered through a pad of CELITE
  4. filtrationfilter agent
  5. washThe pad was rinsed with methanol
  6. concentrationthe combined filtrates were concentrated under reduced pressure
  7. additionThe resulting material was treated with 20 mL of H2O and 2 mL of concentrated NH4OH solution
  8. extractionextracted into CHCl3 (3×25 mL)
  9. concentrationThe combined organic layers were concentrated under reduced pressure
  10. customChromatography (SiO2, 15-30% CMA/CHCl3) gave a white powder
  11. customCrystallization from ethanol/H2O

Sources & evidence

ORD record
ord-00a6f94e86774a09ab3e463e8a3f81da
Source dataset
uspto-grants-2013_01
Patent number
US08343993B2

Reaction notes

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