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

HRID 1257890
Notes
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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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 887MethanolSolvent
HCID 962
Water
Solvent
HCID 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08461330B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes