1033810-70-6

Basic information

• Product Name: [1,2,4]Triazolo[1,5-a]pyridin-7-ol
• Synonyms: [1,2,4]Triazolo[1,5-a]pyridin-7-ol
• CAS NO: 1033810-70-6
• Molecular Formula: C₆H₅N₃O
• Molecular Weight: 135.1234
• EINECS: -0
• Mol File: 1033810-70-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.51±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 2.38±0.53(Predicted)
• CAS DataBase Reference: [1,2,4]Triazolo[1,5-a]pyridin-7-ol(CAS DataBase Reference)
• NIST Chemistry Reference: [1,2,4]Triazolo[1,5-a]pyridin-7-ol(1033810-70-6)
• EPA Substance Registry System: [1,2,4]Triazolo[1,5-a]pyridin-7-ol(1033810-70-6)

Safety Data

• Hazardous Substances Data: 1033810-70-6(Hazardous Substances Data)

Usage

General Description

"[1,2,4]Triazolo[1,5-a]pyridin-7-ol" is a chemical compound with potential use in medicinal chemistry due its structural uniqueness. It is recognized by its distinctive heterocyclic ring system, which includes a triazole and a pyridine ring fused together. The characteristics of this structure, particularly its conjugated system and nitrogen atoms, significantly contribute to its biological activity. It's frequently used moiety in drug discovery due its properties of enhancing solubility, hydrogen-bonding capabilities, and metabolic stability.

Synthetic route

C7H7N3O → [1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6)

Conditions	Yield
With pyridine hydrochloride at 160℃; for 4h;	85.9%

7-(benzyloxy)-[1,2,4]triazolo[1,5-a]pyridine (1033810-72-8) → [1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal In tetrahydrofuran for 16h;
With palladium on activated charcoal; hydrogen In tetrahydrofuran; methanol at 25℃; under 775.743 Torr; for 16h;

2-amino-4-methoxypyridine (10201-73-7) → [1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol / 10 h / Reflux 2: hydroxylamine-O-sulfonic acid; pyridine / methanol / 10 h / Reflux 3: pyridine hydrochloride / 4 h / 160 °C View Scheme

C9H13N3O → [1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydroxylamine-O-sulfonic acid; pyridine / methanol / 10 h / Reflux 2: pyridine hydrochloride / 4 h / 160 °C View Scheme

4-(benzyloxy)pyridin-2-amine (85333-26-2) → [1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: trifluoroacetic acid / ethanol / 16 h / 50 °C 2: hydroxylamine hydrochloride / isopropyl alcohol; tetrahydrofuran / 8 h / 50 °C 3: trifluoroacetic anhydride / tetrahydrofuran / 16 h / 0 - 25 °C 4: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol / 16 h / 25 °C / 775.74 Torr View Scheme

C15H17N3O → [1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride / isopropyl alcohol; tetrahydrofuran / 8 h / 50 °C 2: trifluoroacetic anhydride / tetrahydrofuran / 16 h / 0 - 25 °C 3: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol / 16 h / 25 °C / 775.74 Torr View Scheme

C13H13N3O2 → [1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluoroacetic anhydride / tetrahydrofuran / 16 h / 0 - 25 °C 2: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol / 16 h / 25 °C / 775.74 Torr View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) + 5-nitro-2-fluorotoluene (455-88-9) → 7-(2-methyl-4-nitrophenoxy)-[1,2,4]triazolo[1,5-a]pyridine (937263-44-0)

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 80℃; for 3h;	87%
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 2h;	75%

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) + tert-butyl 3-chloro-2,4-difluorobenzoate (1354962-79-0) → tert-butyl 4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-chloro-2-fluorobenzoate

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 12h;

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → C28H27F2N7O2

Conditions	Yield
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3: acetonitrile / 2 h / Reflux 4: potassium tert-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 16 h / 100 °C View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → (R)-N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-5-((1-ethyl-3,3-difluoropiperidin-4-yl)oxy)quinazolin-4-amine + (S)-N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-5-((1-ethyl-3,3-difluoropiperidin-4-yl)oxy)quinazolin-4-amine

Conditions	Yield
Multi-step reaction with 5 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3: acetonitrile / 2 h / Reflux 4: potassium tert-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 16 h / 100 °C 5: carbon dioxide; diethylamine / ethanol / Resolution of racemate View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → C21H15FN6O

Conditions	Yield
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3: acetonitrile / 2 h / Reflux View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → (S)-N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-5-((3,3-difluoropiperidin-4-yl)oxy)-7-methoxyquinazolin-4-amine hydrogen chloride salt

Conditions	Yield
Multi-step reaction with 5 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3.1: acetic acid / 40 - 60 °C 4.1: potassium tert-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 0.33 h / 20 °C 4.2: 5 h / 90 °C 5.1: hydrogenchloride / water; ethyl acetate / 1 h / 10 °C View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → C21H14F2N6O

Conditions	Yield
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3: potassium tert-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 2 h / 120 °C View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → (R)-N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-5-((3,3-difluoro-1-methylpiperidin-4-yl)oxy)-7-fluoroquinazolin-4-amine + (S)-N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-5-((3,3-difluoro-1-methylpiperidin-4-yl)oxy)-7-fluoroquinazolin-4-amine

Conditions	Yield
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3: potassium tert-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 2 h / 120 °C 4: potassium tert-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 100 °C View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → C27H25F2N7O2 + C27H25F2N7O2

Conditions	Yield
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3: acetonitrile / 2 h / Reflux 4: potassium tert-butylate / N,N-dimethyl-formamide / 16 h / 100 °C View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → C28H27F2N7O2

Conditions	Yield
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3: acetonitrile / 2 h / Reflux 4: potassium tert-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 16 h / 100 °C View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-5-(((1R,5S)-8-(2,2-difluoroethyl)-8-azabicyclo[3.2.1]octan-3-yl)oxy)quinazolin-4-amine

Conditions	Yield
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3: acetonitrile / 2 h / Reflux 4: potassium tert-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 120 h / 90 °C View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-5-(((2S,4S)-5,5-difluoro-1,2-dimethylpiperidin-4-yl)oxy)quinazolin-4-amine + N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-5-(((2R,4R)-5,5-difluoro-1,2-dimethylpiperidin-4-yl)oxy)quinazolin-4-amine

Conditions	Yield
Multi-step reaction with 5 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3: acetonitrile / 2 h / Reflux 4: potassium tert-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 16 h / 100 °C 5: carbon monoxide; diethylamine / ethanol / Resolution of racemate View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3 -methylphenyl)-5-((( 1R,3 s,5 S)-8-methyl-8-azabicyclo[3 .2.1 ]octan-3 -yl)oxy)quinazolin-4-amine

Conditions	Yield
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3: acetonitrile / 2 h / Reflux 4: potassium tert-butylate / N,N-dimethyl-formamide / 120 h / 25 - 90 °C View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → C31H31F2N7O4

Conditions	Yield
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3: acetonitrile / 2 h / Reflux 4: potassium tert-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 16 h / 100 °C View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → C31H31F2N7O4 + C31H31F2N7O4

Conditions	Yield
Multi-step reaction with 5 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3: acetonitrile / 2 h / Reflux 4: potassium tert-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 16 h / 100 °C 5: carbon dioxide / ethanol / Resolution of racemate View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → (±)-N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-5-(((2R,4S)-1-(methyl-d3)-2-(trifluoromethyl)piperidin-4-yl)oxy)quinazolin-4-amine

Conditions	Yield
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3: acetic acid / 1.5 h / 120 °C View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → C21H15FN6O2

Conditions	Yield
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3: acetic acid / 12 h / 50 °C 4: pyridine hydrochloride / 2 h / 170 °C View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → C22H14(2)H3FN6O2

Conditions	Yield
Multi-step reaction with 5 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3: acetic acid / 12 h / 50 °C 4: pyridine hydrochloride / 2 h / 170 °C 5: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → (±)-N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-5-((3,3-difluoro-1-(methyl-d3)piperidin-4-yl)oxy)-6-(methoxy-d3)quinazolin-4-amine

Conditions

Yield

Multi-step reaction with 6 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3.1: acetic acid / 12 h / 50 °C 4.1: pyridine hydrochloride / 2 h / 170 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C 6.1: potassium tert-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 0.5 h / 20 °C 6.2: 12 h / 90 °C View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → C32H32(2)HF2N7O5

Conditions	Yield
Multi-step reaction with 4 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3.1: acetic acid / 40 - 60 °C 4.1: potassium tert-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 4.2: 12 h / 90 °C / Inert atmosphere View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → C27H24(2)HF2N7O3

Conditions

Yield

Multi-step reaction with 5 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3.1: acetic acid / 40 - 60 °C 4.1: potassium tert-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 4.2: 12 h / 90 °C / Inert atmosphere 5.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → (±)-N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-5-((3,3-difluoro-1-methylpiperidin-4-yl-4-d)oxy)-7-methoxyquinazolin-4-amine

Conditions

Yield

Multi-step reaction with 6 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3.1: acetic acid / 40 - 60 °C 4.1: potassium tert-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 4.2: 12 h / 90 °C / Inert atmosphere 5.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 6.1: acetic acid / methanol; dichloromethane / 12 h / 20 °C 6.2: 0.5 h / 20 °C View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → C28H23(2)H4F2N7O3*(x)ClH

Conditions

Yield

Multi-step reaction with 6 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3.1: acetic acid / 40 - 60 °C 4.1: potassium tert-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 4.2: 12 h / 90 °C / Inert atmosphere 5.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 6.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → C28H23(2)H4F2N7O3 + C28H23(2)H4F2N7O3

Conditions

Yield

Multi-step reaction with 7 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3.1: acetic acid / 40 - 60 °C 4.1: potassium tert-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 4.2: 12 h / 90 °C / Inert atmosphere 5.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 6.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 7.1: ammonium hydroxide / Resolution of racemate View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → C32H33F2N7O5

Conditions	Yield
Multi-step reaction with 4 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3.1: acetic acid / 40 - 60 °C 4.1: potassium tert-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 0.33 h / 20 °C 4.2: 5 h / 90 °C View Scheme

[1,2,4]triazolo[1,5-a]pyridin-7-ol (1033810-70-6) → C22H17FN6O2

Conditions	Yield
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 45 °C / 2068.65 Torr 3: acetic acid / 12 h / 50 °C View Scheme

Upstream product

• 1033810-72-8 7-(benzyloxy)-[1,2,4]triazolo[1,5-a]pyridine 
• 10201-73-7 2-amino-4-methoxypyridine 
• 85333-26-2 4-(benzyloxy)pyridin-2-amine 

Downstream Products

• 937263-71-3 4-([1,2,4]triazolo[1,5-α]pyridin-7-yloxy)-3-methylaniline 
• 937263-44-0 7-(2-methyl-4-nitrophenoxy)-[1,2,4]triazolo[1,5-a] pyridine 
• 1033810-73-9 4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-chloroaniline 

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