ethyl 5-[5-(benzyloxycarbonylamidino)furo[2,3-b]pyridine-2-carboxamido]-2-pyridyloxyacetate

Base Information

• Chemical Name: ethyl 5-[5-(benzyloxycarbonylamidino)furo[2,3-b]pyridine-2-carboxamido]-2-pyridyloxyacetate
• CAS No.: 174774-49-3
• Molecular Formula: C₂₆H₂₃N₅O₇
• Molecular Weight: 517.498
• Mol file: 174774-49-3.mol

Synonyms:ethyl 5-[5-(benzyloxycarbonylamidino)furo[2,3-b]pyridine-2-carboxamido]-2-pyridyloxyacetate

Chemical Property of ethyl 5-[5-(benzyloxycarbonylamidino)furo[2,3-b]pyridine-2-carboxamido]-2-pyridyloxyacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 5-[5-(benzyloxycarbonylamidino)furo[2,3-b]pyridine-2-carboxamido]-2-pyridyloxyacetate

There total 7 articles about ethyl 5-[5-(benzyloxycarbonylamidino)furo[2,3-b]pyridine-2-carboxamido]-2-pyridyloxyacetate 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: 45.0%

ethyl 2-(5-aminopyridin-2-yloxy)acetate (203664-68-0) + 5-(benzyloxycarbonylamidino)furo[2,3-b]pyridine-2-carboxylic acid (259150-12-4) → ethyl 5-[5-(benzyloxycarbonylamidino)furo[2,3-b]pyridine-2-carboxamido]-2-pyridyloxyacetate (174774-49-3)

Guidance literature:

With benzotriazol-1-ol; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1248/cpb.47.1694

Reference yield:

ethyl 5-nitrofuro[2,3-b]pyridine-2-carboxylate (6563-64-0) → ethyl 5-[5-(benzyloxycarbonylamidino)furo[2,3-b]pyridine-2-carboxamido]-2-pyridyloxyacetate (174774-49-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 96 percent / H₂ / 10 percent Pd/C / ethanol / 15 h / 20 °C

2.1: 12N aq. HCl; NaNO₂ / tetrahydrofuran / 0.33 h / 2 - 3 °C

2.2: 20 percent / KCN / 3.5 h / 3 - 50 °C

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

4.1: HCl

5.1: NH₃ / ethanol

6.1: aq. NaOH / tetrahydrofuran

7.1: 45 percent / HOBt; EDI / dimethylformamide / 18 h / 20 °C

With hydrogenchloride; lithium hydroxide; sodium hydroxide; ammonia; hydrogen; benzotriazol-1-ol; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Diazotization / 2.2: Sandmeyer reaction / 3.1: Hydrolysis / 4.1: Pinner reaction / 5.1: aminolysis / 6.1: Acylation / 7.1: coupling;

DOI:10.1248/cpb.47.1694

Reference yield:

5-cyanofuro[2,3-b]pyridine-2-carboxylic acid (174775-52-1) → ethyl 5-[5-(benzyloxycarbonylamidino)furo[2,3-b]pyridine-2-carboxamido]-2-pyridyloxyacetate (174774-49-3)

Guidance literature:

Multi-step reaction with 4 steps

1: HCl

2: NH₃ / ethanol

3: aq. NaOH / tetrahydrofuran

4: 45 percent / HOBt; EDI / dimethylformamide / 18 h / 20 °C

With hydrogenchloride; sodium hydroxide; ammonia; benzotriazol-1-ol; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; 1: Pinner reaction / 2: aminolysis / 3: Acylation / 4: coupling;

DOI:10.1248/cpb.47.1694

upstream raw materials:

ethyl 2-(5-aminopyridin-2-yloxy)acetate

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

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

5-cyanofuro[2,3-b]pyridine-2-carboxylic acid