13575-41-2

Usage

Uses

Used in Pharmaceutical Industry:
Thiazolo[4,5-b]pyridin-2-amine is used as a potential drug candidate for its pharmacological properties, such as its antioxidant, antimicrobial, and anticancer activities. Its diverse biological activities make it a promising compound for the development of new drugs and pharmaceuticals.
Used in Medicinal Chemistry Research:
Thiazolo[4,5-b]pyridin-2-amine is used as a subject of research in medicinal chemistry to explore its potential applications and to understand its mechanism of action. Its unique chemical structure and biological activities provide valuable insights for the development of novel therapeutic agents.
Used in Drug Discovery:
Thiazolo[4,5-b]pyridin-2-amine is used as a target for drug discovery efforts, as its potential pharmacological properties and diverse biological activities make it a promising candidate for the development of new therapeutic agents. Further research and development in this area could lead to the discovery of innovative drugs with improved efficacy and safety profiles.

Synthetic route

2-pyridylthiourea (14294-11-2) → [1,3]thiazolo[4,5-b]pyridin-2-amine (13575-41-2)

Conditions	Yield
With bromine In chloroform Heating;	57%

2-aminopyridine (504-29-0) + potassium thioacyanate (333-20-0) → [1,3]thiazolo[4,5-b]pyridin-2-amine (13575-41-2)

Conditions	Yield
With bromine; acetic acid

2-aminopyridine (504-29-0) + methyl halide → [1,3]thiazolo[4,5-b]pyridin-2-amine (13575-41-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / aq. HCl / 6 h / Heating 2: 57 percent / Br2 / CHCl3 / Heating View Scheme

2-Amino-3-bromopyridine (13534-99-1) → [1,3]thiazolo[4,5-b]pyridin-2-amine (13575-41-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: acetone / 14 h / 60 °C 2: sodium hydroxide; water / methanol / 2 h / 70 °C 3: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.14 h / 90 °C View Scheme

C13H10BrN3OS → [1,3]thiazolo[4,5-b]pyridin-2-amine (13575-41-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; water / methanol / 2 h / 70 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.14 h / 90 °C View Scheme

1-(3-bromopyridin-2-yl)thiourea → [1,3]thiazolo[4,5-b]pyridin-2-amine (13575-41-2)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 90℃; for 0.14h;	8.6 g

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + [1,3]thiazolo[4,5-b]pyridin-2-amine (13575-41-2) → 1-{([1,3]thiazolo[4,5-b]pyridin-2-yldiazenyl)oxy}-pyrrolidine-2,5-dione

Conditions	Yield
Stage #1: [1,3]thiazolo[4,5-b]pyridin-2-amine With hydrogenchloride; sodium nitrite at 0 - 5℃; Stage #2: 1-hydroxy-pyrrolidine-2,5-dione With sodium hydroxide at 0 - 5℃; pH=8 - 10;	55%

N-hydroxyphthalimide (524-38-9) + [1,3]thiazolo[4,5-b]pyridin-2-amine (13575-41-2) → 2-{([1,3]thiazolo[4,5-b]pyridin-2-yldiazenyl)oxy}-1H-isoindole-1,3(2H)-dione

Conditions	Yield
Stage #1: [1,3]thiazolo[4,5-b]pyridin-2-amine With hydrogenchloride; sodium nitrite at 0 - 5℃; Stage #2: N-hydroxyphthalimide With sodium hydroxide at 0 - 5℃; pH=8 - 10;	52%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + [1,3]thiazolo[4,5-b]pyridin-2-amine (13575-41-2) → 1-{[1,3]thiazolo[4,5-b]pyridin-2-yloxy}pyrrolidine-2,5-dione

Conditions	Yield
Stage #1: [1,3]thiazolo[4,5-b]pyridin-2-amine With hydrogenchloride; sodium nitrite at 0 - 5℃; Stage #2: 1-hydroxy-pyrrolidine-2,5-dione With sodium hydroxide at 0 - 5℃; pH=10 - 12;	51%

[1,3]thiazolo[4,5-b]pyridin-2-amine (13575-41-2) → thiazolo(4,5-b)pyridine (273-98-3)

Conditions	Yield
With isopentyl nitrite In tetrahydrofuran at 65℃; for 4h;	46.6%

N-hydroxyphthalimide (524-38-9) + [1,3]thiazolo[4,5-b]pyridin-2-amine (13575-41-2) → 2-{[1,3]thiazolo[4,5-b]pyridin-2-yloxy}-1H-isoindole-1,3(2H)-dione

Conditions	Yield
Stage #1: [1,3]thiazolo[4,5-b]pyridin-2-amine With hydrogenchloride; sodium nitrite at 0 - 5℃; Stage #2: N-hydroxyphthalimide With sodium hydroxide at 0 - 5℃; pH=10 - 12;	42%

C35H42N4O4 + [1,3]thiazolo[4,5-b]pyridin-2-amine (13575-41-2) → 3-(5-methyl-1-tricyclo[3.3.1.13,7]decan-1-ylmethyl-1H-pyrazol-4-yl)-6-[8-(thiazolo[4,5-b]pyridin-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-pyridine-2-carboxylic acid tert-butyl ester (1430846-28-8)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;

di(succinimido) carbonate (74124-79-1) + tert-butyl 3-{1-[(3-{[13-(tert-butoxycarbonyl)-2,2,7,7-tetramethyl-10,10-dioxido-3,3-diphenyl-4,9-dioxa-10λ6-thia-13-aza-3-silapentadecan-15-yl]oxy}-5,7-dimethyltricyclo[3.3.1.13'7]dec-1-yl)methyl]-5-methyl-1H-pyrazol-4-yl}-6-(1,2,3,4-tetrahydroquinolin-7-yl)pyridine-2-carboxylate + [1,3]thiazolo[4,5-b]pyridin-2-amine (13575-41-2) → C74H96N8O10S2Si

Conditions	Yield
Stage #1: di(succinimido) carbonate; [1,3]thiazolo[4,5-b]pyridin-2-amine In acetonitrile for 1h; Stage #2: tert-butyl 3-{1-[(3-{[13-(tert-butoxycarbonyl)-2,2,7,7-tetramethyl-10,10-dioxido-3,3-diphenyl-4,9-dioxa-10λ6-thia-13-aza-3-silapentadecan-15-yl]oxy}-5,7-dimethyltricyclo[3.3.1.13'7]dec-1-yl)methyl]-5-methyl-1H-pyrazol-4-yl}-6-(1,2,3,4-tetrahydroquinolin-7-yl)pyridine-2-carboxylate In acetonitrile
Stage #1: di(succinimido) carbonate; [1,3]thiazolo[4,5-b]pyridin-2-amine In acetonitrile at 20℃; for 1h; Stage #2: tert-butyl 3-{1-[(3-{[13-(tert-butoxycarbonyl)-2,2,7,7-tetramethyl-10,10-dioxido-3,3-diphenyl-4,9-dioxa-10λ6-thia-13-aza-3-silapentadecan-15-yl]oxy}-5,7-dimethyltricyclo[3.3.1.13'7]dec-1-yl)methyl]-5-methyl-1H-pyrazol-4-yl}-6-(1,2,3,4-tetrahydroquinolin-7-yl)pyridine-2-carboxylate In acetonitrile

7-[6-(tert-butoxycarbonyl)-5-{1-[(3-{[13-(tert-butoxycarbonyl)-2,2,7,7-tetramethyl-10,10-dioxido-3,3-diphenyl-4,9-dioxa-10 6-thia-13-aza-3-silapentadecan-15-yl]oxy}-5,7-dimethyltricyclo[3.3.1.13'7]dec-1-yl)methyl]-5-methyl-1H-pyrazol-4-yl}pyridin-2-yl]naphthalene-1-carboxylic acid + [1,3]thiazolo[4,5-b]pyridin-2-amine (13575-41-2) → C75H93N7O10S2Si

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane

di(succinimido) carbonate (74124-79-1) + tert-butyl 3-{1-[(3-{[13-(tert-butoxycarbonyl)-2,2,7,7-tetramethyl-10,10-dioxido-3,3-diphenyl-4,9-dioxa-10λ6-thia-13-aza-3-silapentadecan-15-yl]oxy}-5,7-dimethyltricyclo[3.3.1.13'7]dec-1-yl)methyl]-5-methyl-1H-pyrazol-4-yl}-6-(1,2,3,4-tetrahydroquinolin-7-yl)pyridine-2-carboxylate + [1,3]thiazolo[4,5-b]pyridin-2-amine (13575-41-2) → 3-{1-[(3,5-dimethyl-7-{2-[(2-sulfoethyl)amino]ethoxy}tricyclo[3.3.1.13'7]dec-1-yl)methyl]-5-methyl-1H-pyrazol-4-yl}-6-[1-([1,3]thiazolo[4,5-b]pyridin-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl]pyridine-2-carboxylic acid

Conditions

Yield

Stage #1: di(succinimido) carbonate; [1,3]thiazolo[4,5-b]pyridin-2-amine In acetonitrile for 1h; Stage #2: tert-butyl 3-{1-[(3-{[13-(tert-butoxycarbonyl)-2,2,7,7-tetramethyl-10,10-dioxido-3,3-diphenyl-4,9-dioxa-10λ6-thia-13-aza-3-silapentadecan-15-yl]oxy}-5,7-dimethyltricyclo[3.3.1.13'7]dec-1-yl)methyl]-5-methyl-1H-pyrazol-4-yl}-6-(1,2,3,4-tetrahydroquinolin-7-yl)pyridine-2-carboxylate In acetonitrile Stage #3: With trifluoroacetic acid

7-[6-(tert-butoxycarbonyl)-5-{1-[(3-{[13-(tert-butoxycarbonyl)-2,2,7,7-tetramethyl-10,10-dioxido-3,3-diphenyl-4,9-dioxa-10 6-thia-13-aza-3-silapentadecan-15-yl]oxy}-5,7-dimethyltricyclo[3.3.1.13'7]dec-1-yl)methyl]-5-methyl-1H-pyrazol-4-yl}pyridin-2-yl]naphthalene-1-carboxylic acid + [1,3]thiazolo[4,5-b]pyridin-2-amine (13575-41-2) → 3-{1-[(3,5-dimethyl-7-{2-[(2-sulfoethyl)amino]ethoxy}tricyclo[3.3.1.13'7]dec-1-yl)methyl]-5-methyl-1H-pyrazol-4-yl}-6-[8-([1,3]thiazolo[4,5-b]pyridin-2-ylcarbamoyl)naphthalen-2-yl]pyridine-2-carboxylic acid

Conditions

Yield

Stage #1: 7-[6-(tert-butoxycarbonyl)-5-{1-[(3-{[13-(tert-butoxycarbonyl)-2,2,7,7-tetramethyl-10,10-dioxido-3,3-diphenyl-4,9-dioxa-10 6-thia-13-aza-3-silapentadecan-15-yl]oxy}-5,7-dimethyltricyclo[3.3.1.13'7]dec-1-yl)methyl]-5-methyl-1H-pyrazol-4-yl}pyridin-2-yl]naphthalene-1-carboxylic acid; [1,3]thiazolo[4,5-b]pyridin-2-amine With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Stage #2: With trifluoroacetic acid In dichloromethane

Upstream product

• 504-29-0 2-aminopyridine 
• 333-20-0 potassium thioacyanate 
• 14294-11-2 2-pyridylthiourea 
• 13534-99-1 2-Amino-3-bromopyridine 

Downstream Products

• 273-98-3 thiazolo(4,5-b)pyridine 

Relevant academic research and scientific papers

The synthesis and antimicrobial screening of some novel aza-imidoxy compounds as potential chemotherapeutic agents

Some novel azaimidoxy compounds viz. 2-{[(4-chlorophenyl)diazenyl]oxy}-1H -isoindole-1,3-(2H )-dione (Va), and 1-{[1-naphthyldiazenyl]oxy}pyrrolidine-2,5- dione (IVc), etc. have been synthesized by a simple diazotization reaction followed by a coupling with 2-hydroxy-1H -isoindole-1,3(2H )-dione (III)/1-hydroxypyrrolidine-2,5-dione (II) of corresponding aromatic primary amine derivatives at a suitable pH. A similar reaction with a [1,3]thiazolo[4,5- b ]pyridin-2-amine (VIII) lead us to some interesting results variable with a pH. The structure of all synthesized compounds has been established by IR, 1H NMR, and mass studies. These compounds have been screened for antimicrobial activities in order to evaluate the possibility of the derivatives to be used as potential chemotherapeutic agents. Copyright Taylor & Francis Group, LLC.

A thiazole pyridine compound and its preparation method

The invention relates to a thiazole pyridine compound and its preparation method. The compound is thiazolo(4,5-b)pyridine. The preparation method comprises the following steps: (1) a compound 13-bromine-2-aminopyridine is used as a starting material to react in the presence of benzoyl chloride and ammonium thiocyanate so as to obtain a benzoyl-protected thiourea-containing derivative compound 2; (2) the compound 2 undergoes hydrolysis to obtain a thiourea derivative compound; (3) the compound 3 undergoes ring closure under the action of NaH to generate a compound 4; and (4) the compound 4 undergoes deamination by the use of isoamyl nitrite to obtain a target product compound 5. According to the method, raw materials are cheap and easily available. The synthetic method is simple. The preparation method meets requirements of large-scale industrial production.