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

HRID 500234Notes

Reaction equation

HRID 500234 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-57362809b4ef40d2bb5e58aafc65d3b5
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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