Hydrochloric Acid → N-(1-((6-(2-aminoethoxy)pyridin-2-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride

HRID 79282Notes

Reaction equation

HRID 79282 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[N:30]=[C:29]([O:31][CH2:32][CH2:33][NH:34]C(=O)OC(C)(C)C)[CH:28]=[CH:27][CH:26]=2)[N:4]=1)[CH3:2].[ClH:42]>C(OCC)(=O)C>[ClH:42].[ClH:42].[NH2:34][CH2:33][CH2:32][O:31][C:29]1[N:30]=[C:25]([CH2:24][N:5]2[C:6]3[C:11](=[C:10]([NH:12][C:13]([C:15]4[N:19]5[CH:20]=[CH:21][CH:22]=[CH:23][C:18]5=[N:17][CH:16]=4)=[O:14])[CH:9]=[CH:8][CH:7]=3)[C:3]([CH2:1][CH3:2])=[N:4]2)[CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67261301tert-butyl 2-(6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yloxy)ethylcarbamate

Product 1

HCID 67259273N-(1-((6-(2-aminoethoxy)pyridin-2-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide dihydrochlorideYield 69%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 2-(6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yloxy)ethylcarbamate (21.9 mg, 0.0394 mmol) in ethyl acetate was added hydrogen chloride (1 mL; 4M in dioxane). The mixture was stirred for 30 minutes and the solvent was removed under reduced pressure to give N-(1-((6-(2-aminoethoxy)pyridin-2-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride (14.3 mg; 69%). MS (APCI), positive scan, m/z=456.1 (M+H).

Workup

  1. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a537ea5ab4544afb833558ed84a3d710
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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