Ethyl 5-aminofuro[2,3-b]pyridine-2-carboxylate

Base Information

• Chemical Name: Ethyl 5-aminofuro[2,3-b]pyridine-2-carboxylate
• CAS No.: 6562-74-9
• Molecular Formula: C10H10N2O3
• Molecular Weight: 206.201
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID40441731
• Mol file: 6562-74-9.mol

Synonyms:Ethyl 5-aminofuro[2,3-b]pyridine-2-carboxylate;6562-74-9;Furo[2,3-b]pyridine-2-carboxylic acid, 5-amino-, ethyl ester;DTXSID40441731;AKOS015910168;FT-0645531;A835163;5-Aminofuro[2,3-b]pyridine-2-carboxylic acid ethyl ester;Furo[2,3-b]pyridine-2-carboxylic acid,5-amino-,ethyl ester

Chemical Property of Ethyl 5-aminofuro[2,3-b]pyridine-2-carboxylate

Chemical Property:

• Melting Point: 176-177 °C
• Boiling Point: 350.353 °C at 760 mmHg
• PKA: 3.48±0.40(Predicted)
• Flash Point: 165.688 °C
• PSA: 78.35000
• Density: 1.32 g/cm³
• LogP: 2.16790
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 206.06914219
• Heavy Atom Count: 15
• Complexity: 247

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl5-aminofuro[2,3-b]pyridine-2-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=CC(=CN=C2O1)N

Technology Process of Ethyl 5-aminofuro[2,3-b]pyridine-2-carboxylate

There total 2 articles about Ethyl 5-aminofuro[2,3-b]pyridine-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

ethyl 5-nitrofuro[2,3-b]pyridine-2-carboxylate (6563-64-0) → ethyl 5-aminofuro[2,3-b]pyridine-2-carboxylate (6562-74-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 15h;

DOI:10.1248/cpb.47.1694

Reference yield:

ethyl 2-amino-furan-5-carboxylate (15856-35-6) → ethyl 5-aminofuro[2,3-b]pyridine-2-carboxylate (6562-74-9)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. HCl / aq. ethanol

2: H₂ / Pd-C / ethanol

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol;

Reference yield:

ethyl 5-aminofuro[2,3-b]pyridine-2-carboxylate (6562-74-9) → ethyl trans-3-[4-(5-amidinofuro[2,3-b]pyridine-2-carboxamido)cyclohexyl]propionate (259150-40-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 12N aq. HCl; NaNO₂ / tetrahydrofuran / 0.33 h / 2 - 3 °C

1.2: 20 percent / KCN / 3.5 h / 3 - 50 °C

2.1: aq. LiOH / tetrahydrofuran / 1 h / 20 °C

3.1: HCl

4.1: NH₃ / ethanol

5.1: aq. NaOH / tetrahydrofuran

6.1: 59 percent / HOBt; EDI / dimethylformamide / 18 h / 20 °C

7.1: 48 percent / HCl; H₂ / 10 percent Pd/C / CHCl₃; ethanol / 14 h / 20 °C

With hydrogenchloride; lithium hydroxide; sodium hydroxide; ammonia; hydrogen; benzotriazol-1-ol; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; ethanol; chloroform; N,N-dimethyl-formamide; 1.1: Diazotization / 1.2: Sandmeyer reaction / 2.1: Hydrolysis / 3.1: Pinner reaction / 4.1: aminolysis / 5.1: Acylation / 6.1: coupling / 7.1: Hydrogenolysis;

DOI:10.1248/cpb.47.1694

upstream raw materials:

ethyl 5-nitrofuro[2,3-b]pyridine-2-carboxylate

ethyl 2-amino-furan-5-carboxylate

Downstream raw materials:

5-(benzyloxycarbonylamidino)furo[2,3-b]pyridine-2-carboxylic acid

t-Butyl 4-(5-cyanofuro[2,3-b]pyridine-2-carbonylamino)phenoxy-acetate

{4-[(5-methylsulfanylcarbonimidoyl-furo[2,3-b]pyridine-2-carbonyl)-amino]-phenoxy}-acetic acid tert-butyl ester

{4-[(5-mercaptocarbonimidoyl-furo[2,3-b]pyridine-2-carbonyl)-amino]-phenoxy}-acetic acid tert-butyl ester

Refernces