Hydrochloric Acid → 1-(2-aminoethyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c][1,5]naphthyridine-4-amine hydrochloride

HRID 81895Notes

Reaction equation

HRID 81895 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[N:13]=[C:14]([CH2:26][CH2:27][O:28][CH3:29])[N:15]([CH2:16][CH2:17][NH:18]C(=O)OC(C)(C)C)[C:11]=2[C:10]2[N:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]=1.[Cl:30]CCl.CO>O1CCOCC1>[ClH:30].[NH2:18][CH2:17][CH2:16][N:15]1[C:11]2[C:10]3[N:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[C:3]([NH2:2])[C:12]=2[N:13]=[C:14]1[CH2:26][CH2:27][O:28][CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226129Dichloromethane methanolHCID 68933229HCID 68933229, compound

Product 1

HCID 689332551-(2-aminoethyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c][1,5]naphthyridine-4-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of hydrochloric acid in dioxane (58 mL of 4 M) was added to a solution of tert-butyl N-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]ethyl}carbamate (3 g) in a small amount of dichloromethane/methanol. The reaction mixture was stirred overnight at ambient temperature and then concentrated under reduced pressure to provide 3.7 g of crude 1-(2-aminoethyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c][1,5]naphthyridine-4-amine hydrochloride.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-668bb8bd18e4480db413ff5e7b12a298
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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