Reaction #166466

ord-67bbe38da9804b279014e204fa18e915

Reaction equation

CCc1nn(Cc2cccc(OCCCNC(=O)OC(C)(C)C)n2)c2cccc(NC(=O)c3cnc4ccccn34)c12
tert-butyl 3-(6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yloxy)propylcarbamate
Cl
hydrogen chloride
→
CCc1nn(Cc2cccc(OCCCN)n2)c2cccc(NC(=O)c3cnc4ccccn34)c12.Cl.Cl
N-(1-((6-(3-aminopropoxy)pyridin-2-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride

Reactants

CCc1nn(Cc2cccc(OCCCNC(=O)OC(C)(C)C)n2)c2cccc(NC(=O)c3cnc4ccccn34)c12
tert-butyl 3-(6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yloxy)propylcarbamate
Cl
hydrogen chloride

Reagents

None

Solvents

CCOC(C)=O
ethyl acetate

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe solvent was removed under reduced pressure

Procedure

To a solution of tert-butyl 3-(6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yloxy)propylcarbamate (17.2 mg, 0.0302 mmol) in ethyl acetate was added hydrogen chloride (1 mL; 4M in dioxane). The mixture was stirred for 30 minutes. The solvent was removed under reduced pressure to give N-(1-((6-(3-aminopropoxy)pyridin-2-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride (11.6 mg). MS (APCI), positive scan, m/z=470.1 (M+H).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08841455B2uspto-grants-2014_09