Hydrochloric Acid → 4-[7-(1-Quinolin-6-ylethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzoic acid

HRID 1257890Notes

Reaction equation

HRID 1257890 reaction equation
O.[OH-].[Li+].[N:4]1[C:13]2[C:8](=[CH:9][C:10]([CH:14]([C:16]3[N:20]4[N:21]=[C:22]([C:25]5[CH:34]=[CH:33][C:28]([C:29]([O:31]C)=[O:30])=[CH:27][CH:26]=5)[CH:23]=[N:24][C:19]4=[N:18][CH:17]=3)[CH3:15])=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1.Cl>C1COCC1.CO.O>[N:4]1[C:13]2[C:8](=[CH:9][C:10]([CH:14]([C:16]3[N:20]4[N:21]=[C:22]([C:25]5[CH:34]=[CH:33][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=5)[CH:23]=[N:24][C:19]4=[N:18][CH:17]=3)[CH3:15])=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67225068Methyl 4-[7-(1-quinolin-6-ylethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzoate

Product 1

HCID 672239824-[7-(1-Quinolin-6-ylethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (24 mg, 0.57 mmol) was added to a solution of methyl 4-[7-(1-quinolin-6-ylethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzoate (47 mg, 0.115 mmol) in THF (0.5 mL) and methanol (0.5 mL) and water (0.2 mL). The mixture was stirred at RT for 2 h. LCMS showed the reaction was complete. The mixture was adjusted with conc. HCl to pH 2. The volatiles were removed under reduced pressure to provide the crude product which was directly used in next step. LCMS: (M+H)=396.1.

Workup

  1. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-bff7e5cd576d4d0f93309ee7d2aa6816
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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