5093-64-1

Usage

Chemical Properties

Gray Solid

InChI:InChI=1/C7H7N3O3/c1-5(11)9-7-3-2-6(4-8-7)10(12)13/h2-4H,1H3,(H,8,9,11)

Synthetic route

5-nitro-pyridin-2-ylamine (4214-76-0) → N-(5-aminopyridin-2-yl)acetamide (29958-14-3) + 2-acetamido-5-nitropyridine (5093-64-1)

Conditions	Yield
With sulfuric acid In acetic anhydride	A n/a B 98%

5-nitro-pyridin-2-ylamine (4214-76-0) + acetic anhydride (108-24-7) → 2-acetamido-5-nitropyridine (5093-64-1)

Conditions	Yield
With pyridine; dmap at 0 - 20℃;	86%
With pyridine; dmap at 0 - 25℃; for 5h;	86%
at 130℃; for 1.5h;	81%

5-nitro-pyridin-2-ylamine (4214-76-0) + acetyl chloride (75-36-5) → 2-acetamido-5-nitropyridine (5093-64-1)

Conditions	Yield
With pyridine In tetrahydrofuran at 0 - 20℃; for 2h;	80.1%
With triethylamine In dichloromethane at 20℃; for 6h;	77%
With dmap; triethylamine In tetrahydrofuran; ethyl acetate
With dmap; triethylamine In tetrahydrofuran for 24h; Heating / reflux;

5-nitro-pyridin-2-ylamine (4214-76-0) + N,N-dimethyl acetamide (127-19-5) → 2-acetamido-5-nitropyridine (5093-64-1)

Conditions	Yield
Stage #1: N,N-dimethyl acetamide With 1,1'-carbonyldiimidazole at 120 - 125℃; for 0.5h; Inert atmosphere; Stage #2: 5-nitro-pyridin-2-ylamine at 60 - 65℃; for 5.5h; Inert atmosphere;	70%

dmap (1122-58-3) + 5-nitro-pyridin-2-ylamine (4214-76-0) + acetyl chloride (75-36-5) → 2-acetamido-5-nitropyridine (5093-64-1)

Conditions	Yield
With potassium carbonate; triethylamine In dichloromethane	49%
With potassium carbonate; triethylamine In dichloromethane	49%

acetamide (60-35-5) + 3-nitropyridine (2530-26-9) → 2-acetamido-5-nitropyridine (5093-64-1)

Conditions	Yield
Stage #1: acetamide With sodium hydride In dimethyl sulfoxide for 2h; Stage #2: 3-nitropyridine With potassium hexacyanoferrate(III) In dimethyl sulfoxide at 20℃; for 2h;	34%

5-nitro-pyridin-2-ylamine (4214-76-0) + acetyl chloride (75-36-5) → 2-acetamido-5-nitropyridine (5093-64-1)

Conditions	Yield
With dmap; N2; triethylamine In CH2C12

2-acetamido-5-nitropyridine (5093-64-1) → N-(5-aminopyridin-2-yl)acetamide (29958-14-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol for 3.5h;	98%
With water; ammonium chloride; zinc In ethanol at 20℃; for 5h;	84%
With hydrogen; palladium on activated charcoal In methanol

methanol (67-56-1) + 2-acetamido-5-nitropyridine (5093-64-1) → N-(5-aminopyridin-2-yl)acetamide (29958-14-3)

Conditions	Yield
In ethanol; chloroform	20%
In ethanol; chloroform	20%

2-acetamido-5-nitropyridine (5093-64-1) + acetic acid (64-19-7) + iron → 5-amino-2-acetylamino-pyridine

2-acetamido-5-nitropyridine (5093-64-1) + sodium chlorodifluoroacetate (1895-39-2) → N-(1-difluoromethyl-5-nitro-1H-pyridin-2-ylidene)-acetamide

Conditions	Yield
With 18-crown-6 ether In acetonitrile for 32h; Heating;

2-acetamido-5-nitropyridine (5093-64-1) → 1-(difluoromethyl)-5-nitropyridin-2(1H)-one

Conditions	Yield
Multi-step reaction with 2 steps 1: 18-crown-6 / acetonitrile / 32 h / Heating 2: aq. KHSO4; 18-crown-6; sodium chlorodifluoroacetate / acetonitrile / 1 h / Heating View Scheme

2-acetamido-5-nitropyridine (5093-64-1) + toluene-4-sulfonic acid (104-15-4) → C7H7N3O3*C7H8O3S (1449012-40-1)

Conditions	Yield
In toluene for 2h; Reflux;

2-acetamido-5-nitropyridine (5093-64-1) → N-(6-acetylaminopyridin-3-yl)-2-aminopyrazolo[1,5-a]pyrimidine-3-carboxamide

Conditions	Yield
Multi-step reaction with 2 steps 1.1: zinc; ammonium chloride; water / ethanol / 5 h / 20 °C 2.1: thionyl chloride; triethylamine / dichloromethane / 4 h / 20 °C 2.2: 20 °C View Scheme

2-acetamido-5-nitropyridine (5093-64-1) → aqueous citric acid

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogen; palladium 10% on activated carbon / methanol / 6 h / 2585.81 Torr 2.1: sodium nitrite; hydrogenchloride / water / 0.75 h / 0 °C 2.2: 16 h / 0 - 20 °C 3.1: triethylamine / ethanol / 3 h / pH 9.5 / Reflux View Scheme

2-acetamido-5-nitropyridine (5093-64-1) → N-{4-[5-(acetylamino)-1H-pyrrolo[3,2-b]pyridin-2-yl]phenyl}-1-(phenylacetyl)-L-prolinamide (1246468-33-6)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: hydrogen; palladium 10% on activated carbon / methanol / 6 h / 2585.81 Torr 2.1: sodium nitrite; hydrogenchloride / water / 0.75 h / 0 °C 2.2: 16 h / 0 - 20 °C 3.1: triethylamine / ethanol / 3 h / pH 9.5 / Reflux 4.1: polyphosphoric acid / 1.25 h / 90 °C / Inert atmosphere 5.1: hydrogenchloride; water / 2 h / Reflux 6.1: HATU; N-ethyl-N,N-diisopropylamine / acetonitrile / 25 °C 7.1: triethylamine / acetonitrile / 0.6 h / 0 - 25 °C View Scheme

2-acetamido-5-nitropyridine (5093-64-1) → C7H10N4O (769912-56-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogen; palladium 10% on activated carbon / methanol / 6 h / 2585.81 Torr 2.1: sodium nitrite; hydrogenchloride / water / 0.75 h / 0 °C 2.2: 16 h / 0 - 20 °C View Scheme

2-acetamido-5-nitropyridine (5093-64-1) → C17H16N4O2 (1246470-71-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogen; palladium 10% on activated carbon / methanol / 6 h / 2585.81 Torr 2.1: sodium nitrite; hydrogenchloride / water / 0.75 h / 0 °C 2.2: 16 h / 0 - 20 °C 3.1: triethylamine / ethanol / 3 h / pH 9.5 / Reflux 4.1: polyphosphoric acid / 1.25 h / 90 °C / Inert atmosphere View Scheme

2-acetamido-5-nitropyridine (5093-64-1) → C13H12N4 (1246470-72-3)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: hydrogen; palladium 10% on activated carbon / methanol / 6 h / 2585.81 Torr 2.1: sodium nitrite; hydrogenchloride / water / 0.75 h / 0 °C 2.2: 16 h / 0 - 20 °C 3.1: triethylamine / ethanol / 3 h / pH 9.5 / Reflux 4.1: polyphosphoric acid / 1.25 h / 90 °C / Inert atmosphere 5.1: hydrogenchloride; water / 2 h / Reflux View Scheme

2-acetamido-5-nitropyridine (5093-64-1) → C26H25N5O2 (1246470-73-4)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: hydrogen; palladium 10% on activated carbon / methanol / 6 h / 2585.81 Torr 2.1: sodium nitrite; hydrogenchloride / water / 0.75 h / 0 °C 2.2: 16 h / 0 - 20 °C 3.1: triethylamine / ethanol / 3 h / pH 9.5 / Reflux 4.1: polyphosphoric acid / 1.25 h / 90 °C / Inert atmosphere 5.1: hydrogenchloride; water / 2 h / Reflux 6.1: HATU; N-ethyl-N,N-diisopropylamine / acetonitrile / 25 °C View Scheme

Upstream product

• 4214-76-0 5-nitro-pyridin-2-ylamine 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 60-35-5 acetamide 
• 2530-26-9 3-nitropyridine 
• 127-19-5 N,N-dimethyl acetamide 
• 1122-58-3 dmap 

Downstream Products

• 29958-14-3 N-(5-aminopyridin-2-yl)acetamide 
• 1449012-40-1 C₇H₇N₃O₃*C₇H₈O₃S 

Relevant academic research and scientific papers

INHIBITORS OF HEPATITIS C VIRUS REPLICATION

The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

Synthesis of Amides by Nucleophilic Substitution of Hydrogen in 3-Nitropyridine

3-Nitropyridine reacted with nitrogen-centered carboxylic acid amide anions in anhydrous DMSO in the presence of K3Fe(CN)6 via oxidative nucleophilic substitution of hydrogen to give previously unknown N-(5-nitropyridin-2-yl) carboxa

Pyridines IRAK4 inhibitors, preparation method and application thereof (by machine translation)

The invention belongs to the field of medicine, in particular to a formula (I) of the structural features of pyridine of compound or its pharmaceutically acceptable salt, preparation method thereof, and their use as IRAK4 inhibitors. Experimental results show that, the compound of the invention IRAK4 has prominent inhibit function, can be used for the treatment of autoimmune disease, inflammatory disease, cancer, autoimmune disease and thromboembolism as heterogeneous. (by machine translation)

Convenient N-acetylation of amines in N,N-dimethylacetamide with N,N-carbonyldiimidazole

Dimethylacetamide (DMAc) acts as an efficient source of acetyl and dimethylamine gas in the presence of N,N-carbonyldiimidazole (CDI). Addition of amines to the reaction mixture delivers the corresponding amides in good to excellent yields. The acetylation of amines reported herein, which relies on the in situ generation of N-acetylimidazole on warming of DMAc with CDI at 120-125 °C, serves as a convenient alternative to other acetylation methods.

Esterification catalysis by pyridinium p -toluenesulfonate revisited - Modification with a lipid chain for improved activities and selectivities

The lipid analogs of pyridinium p-toluenesulfonate (PPTS) were examined for catalysis of the condensation of an equimolar mixture of carboxylic acids and alcohols under mild conditions without removal of water. Although PPTS is a poor catalyst, the introduction of a lipid chain and nitro group significantly improved the activity of PPTS and led to selectivity at suppressing the elimination side reactions of alcohols. 2-Oleamido-5-nitro-pyridinium p-toluenesulfonate (6) is a lead catalyst that promoted various esterification reactions with yields up to 99%.

INHIBITORS OF HEPATITIS C VIRUS REPLICATION

The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

QUINOLINE DERIVATIVES FOR MODULATING DNA METHYLATION

Quinoline derivatives, particularly 4-anilinoquinoline derivatives, are provided. Such quinoline derivatives can be used for modulation of DNA methylation, such as effective inhibition of methylation of cytosine at the C-5 position, for example via selective inhibition of DNA methyltransferase DNMT1. Methods for synthesizing numerous 4-anilinoquinoline derivatives and for modulating DNA methylation are provided. Also provided are methods for formulating and administering these compounds or compositions to treat conditions such as cancer and hematological disorders.

AMIDE COMPOUND

There is provided a FAAH inhibitor and a prophylactic or therapeutic agent for cerebrovascular disorders or sleep disorders comprising it. The prophylactic or therapeutic agent comprises a compound of the formula (I0): wherein Z is oxygen or sulfur; R1 is aryl which may be substituted, or a heterocyclic group which may be substituted; R1a is a hydrogen atom, a hydrocarbon group which may be substituted, hydroxyl, etc.; R2 is piperidin-1,4-diyl which may be substituted, or piperazin-1,4-diyl which may be substituted; R3 is a group formed by eliminating two hydrogen atoms from a 5-membered aromatic heterocyclic group having 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur, which may be further substituted, -CO-, etc.; and R4 is a hydrocarbon group which may be substituted, or a heterocyclic group which may be substituted; or a salt thereof.

Thiazolidinones, their production and use as pharmaceutical agents

Thiazolidinones of general formula I in which Q, A, B, X, R1 and R2 have the meanings that are indicated in the description, as well as those of general formula IA in which Q, A, B, X, R1 and R2a have the meanings that are indicated in the description, their production and use as inhibitors of the polo-like kinase (PLK) for treating various diseases as well as intermediate products for the production of thiazolidinones are described.