13575-41-2

Basic information

• Product Name: thiazolo[4,5-b]pyridin-2-amine
• Synonyms: thiazolo[4,5-b]pyridin-2-amine;2-Aminothiazolo[4,5-b]pyridine
• CAS NO: 13575-41-2
• Molecular Formula: C₆H₅N₃S
• Molecular Weight: 151.189
• Mol File: 13575-41-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 239-242℃
• Boiling Point: 329℃
• Flash Point: 153℃
• Appearance: /
• Density: 1.485
• PKA: 1.92±0.50(Predicted)
• CAS DataBase Reference: thiazolo[4,5-b]pyridin-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: thiazolo[4,5-b]pyridin-2-amine(13575-41-2)
• EPA Substance Registry System: thiazolo[4,5-b]pyridin-2-amine(13575-41-2)

Safety Data

• Hazardous Substances Data: 13575-41-2(Hazardous Substances Data)

Usage

General Description

Thiazolo[4,5-b]pyridin-2-amine, also known as TAZOPANAM, is a chemical compound with the molecular formula C7H6N4S. It belongs to the class of thiazole compounds, which are well known for their diverse biological activities. Thiazolo[4,5-b]pyridin-2-amine has been studied for its potential pharmacological properties, including its ability to act as an antioxidant, antimicrobial, and anticancer agent. Thiazolo[4,5-b]pyridin-2-amine has also been investigated for its potential application in the development of new drugs and pharmaceuticals. Its unique chemical structure and potential biological activities make thiazolo[4,5-b]pyridin-2-amine an interesting target for further research and development in the field of medicinal chemistry and drug discovery.

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

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

Downstream Products

• 273-98-3 thiazolo(4,5-b)pyridine 

Relevant articles and documents

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.