Hydrochloric Acid → HCID 178511323, compound

HRID 2192235Notes

Reaction equation

HRID 2192235 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([O:25]CC)[N:14]([CH2:15][CH2:16][NH:17]C(=O)OC(C)(C)C)[C:10]=2[C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.Cl>CO.O1CCOCC1>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([OH:25])[N:14]([CH2:15][CH2:16][NH2:17])[C:10]=2[C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69023498HCID 69023498, compound

Product 1

HCID 178511323HCID 178511323, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 2-(4-amino-2-ethoxy-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethylcarbamate (6 g, 16 mmol) in methanol (25 mL) was combined with a solution of hydrogen chloride in dioxane (102 mL of 4N). The reaction mixture was allowed to stir over night at ambient temperature and was then concentrated under reduced pressure to provide crude product as an orange solid. The solid was loaded onto a silica gel column. The column was eluted with 47.5% methanol/2.5% ammonium hydroxide in dichloromethane. The fractions were combined and concentrated under reduced pressure to provide an orange solid. The solid was triturated with hot acetonitrile and methanol and then allowed to cool. The solid was isolated by filtration and then washed sequentially with acetonitrile and diethyl ether to provide 3.5 g of 4-amino-1-(2-aminoethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-ol.

Workup

  1. concentrationwas then concentrated under reduced pressure
  2. customto provide crude product as an orange solid
  3. washThe column was eluted with 47.5% methanol/2.5% ammonium hydroxide in dichloromethane
  4. concentrationconcentrated under reduced pressure
  5. customto provide an orange solid
  6. customThe solid was triturated with hot acetonitrile and methanol
  7. temperatureto cool
  8. customThe solid was isolated by filtration
  9. washwashed sequentially with acetonitrile and diethyl ether

Sources & evidence

ORD record
ord-68789b2e44aa4b36955a34cec1f1b7a2
Source dataset
uspto-grants-2012_12
Patent number
US08329721B2

Reaction notes

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