{4-[3-(3-benzyloxy-propoxy)-phenyl]-1-butyl-2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl}-carbamic acid phenyl ester

Base Information

• Chemical Name: {4-[3-(3-benzyloxy-propoxy)-phenyl]-1-butyl-2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl}-carbamic acid phenyl ester
• CAS No.: 455288-42-3
• Molecular Formula: C₃₅H₃₅N₃O₅
• Molecular Weight: 577.68
• Mol file: 455288-42-3.mol

Synonyms:

Chemical Property of {4-[3-(3-benzyloxy-propoxy)-phenyl]-1-butyl-2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl}-carbamic acid phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {4-[3-(3-benzyloxy-propoxy)-phenyl]-1-butyl-2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl}-carbamic acid phenyl ester

There total 11 articles about {4-[3-(3-benzyloxy-propoxy)-phenyl]-1-butyl-2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl}-carbamic acid phenyl ester 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:

1-[3-(benzyloxy)propoxy]-3-bromobenzene (458558-10-6) → {4-[3-(3-benzyloxy-propoxy)-phenyl]-1-butyl-2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl}-carbamic acid phenyl ester (455288-42-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Mg; I₂ / tetrahydrofuran / 1.5 h / Heating

1.2: 51 percent / B(OMe)3 / tetrahydrofuran / -10 - 20 °C

2.1: 86 percent / cesium carbonate / Pd(PPh₃)4 / dioxane / 4 h / Heating

3.1: 100 percent / zinc; AcOH / methanol / 1.5 h / Heating

4.1: tetrahydrofuran / 20 °C

With iodine; caesium carbonate; magnesium; acetic acid; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; 2.1: Suzuki reaction;

DOI:10.1016/j.tet.2005.08.009

Reference yield:

{3-[3-(benzyloxy)propoxy]phenyl}boronic acid (476370-99-7) → {4-[3-(3-benzyloxy-propoxy)-phenyl]-1-butyl-2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl}-carbamic acid phenyl ester (455288-42-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / cesium carbonate / Pd(PPh₃)4 / dioxane / 4 h / Heating

2: 100 percent / zinc; AcOH / methanol / 1.5 h / Heating

3: tetrahydrofuran / 20 °C

With caesium carbonate; acetic acid; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; 1: Suzuki reaction;

DOI:10.1016/j.tet.2005.08.009

Reference yield:

2-chloronicotinic acid (2942-59-8) → {4-[3-(3-benzyloxy-propoxy)-phenyl]-1-butyl-2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl}-carbamic acid phenyl ester (455288-42-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / 48 h / Heating

2: 66 percent / acetic acid / 2 h / Heating

3: 92 percent / HNO₃; H₂SO₄ / 20 °C

4: 86 percent / POCl₃ / 0.75 h / 100 °C

5: 86 percent / cesium carbonate / Pd(PPh₃)4 / dioxane / 4 h / Heating

6: 100 percent / zinc; AcOH / methanol / 1.5 h / Heating

7: tetrahydrofuran / 20 °C

With sulfuric acid; nitric acid; caesium carbonate; acetic acid; zinc; trichlorophosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; 2: Friedlaender reaction / 5: Suzuki reaction;

DOI:10.1016/j.tet.2005.08.009

upstream raw materials:

3-amino-4-{3-[3-(benzyloxy)propoxy]phenyl}-1-butyl-1,8-naphthyridin-2(1H)-one

phenyl chloroformate

1-[3-(benzyloxy)propoxy]-3-bromobenzene

{3-[3-(benzyloxy)propoxy]phenyl}boronic acid

Downstream raw materials:

tert-butyl [4-({[(4-{3-[3-(benzyloxy)propoxy]phenyl}-1-butyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl)amino]carbonyl}amino)-3,5-diisopropylphenyl]carbamate

tert-butyl (4-{[({1-butyl-4-[3-(3-hydroxypropoxy)phenyl]-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl}-amino)carbonyl]amino}-3,5-diisopropylphenyl)carbamate