Carbamic acid, [4-[[[[1-butyl-1,2-dihydro-2-oxo-4-[3-[3-(phenylmethoxy)propoxy]phenyl]- 1,8-naphthyridin-3-yl]amino]carbonyl]amino]-3,5-bis(1-methylethyl)phen yl]-, 1,1-dimethylethyl ester

Base Information

• Chemical Name: Carbamic acid, [4-[[[[1-butyl-1,2-dihydro-2-oxo-4-[3-[3-(phenylmethoxy)propoxy]phenyl]- 1,8-naphthyridin-3-yl]amino]carbonyl]amino]-3,5-bis(1-methylethyl)phen yl]-, 1,1-dimethylethyl ester
• CAS No.: 476371-02-5
• Molecular Formula: C46H57N5O6
• Molecular Weight: 775.988
• Mol file: 476371-02-5.mol

Synonyms:

Chemical Property of Carbamic acid, [4-[[[[1-butyl-1,2-dihydro-2-oxo-4-[3-[3-(phenylmethoxy)propoxy]phenyl]- 1,8-naphthyridin-3-yl]amino]carbonyl]amino]-3,5-bis(1-methylethyl)phen yl]-, 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbamic acid, [4-[[[[1-butyl-1,2-dihydro-2-oxo-4-[3-[3-(phenylmethoxy)propoxy]phenyl]- 1,8-naphthyridin-3-yl]amino]carbonyl]amino]-3,5-bis(1-methylethyl)phen yl]-, 1,1-dimethylethyl ester

There total 16 articles about Carbamic acid, [4-[[[[1-butyl-1,2-dihydro-2-oxo-4-[3-[3-(phenylmethoxy)propoxy]phenyl]- 1,8-naphthyridin-3-yl]amino]carbonyl]amino]-3,5-bis(1-methylethyl)phen yl]-, 1,1-dimethylethyl 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) → 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 (476371-02-5)

Guidance literature:

Multi-step reaction with 5 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

5.1: 456 mg / DMAP / dimethylformamide / 20 °C

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

DOI:10.1016/j.tet.2005.08.009

Reference yield:

{3-[3-(benzyloxy)propoxy]phenyl}boronic acid (476370-99-7) → 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 (476371-02-5)

Guidance literature:

Multi-step reaction with 4 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

4: 456 mg / DMAP / dimethylformamide / 20 °C

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

DOI:10.1016/j.tet.2005.08.009

Reference yield:

2-chloronicotinic acid (2942-59-8) → 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 (476371-02-5)

Guidance literature:

Multi-step reaction with 8 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

8: 456 mg / DMAP / dimethylformamide / 20 °C

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

DOI:10.1016/j.tet.2005.08.009

upstream raw materials:

tert-butyl (4-amino-3,5-diisopropylphenyl)carbamate

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

4-amino-2,6-diisopropylaniline

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

Downstream raw materials:

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