N-[3,5-bis(trifluoromethyl)benzyl]-7,8-dihydro-7-(2-hydroxyethyl)-5-(4-methylphenyl)-8-oxo-1,7-naphthyridine-6-carboxamide

Base Information

Chemical Name:N-[3,5-bis(trifluoromethyl)benzyl]-7,8-dihydro-7-(2-hydroxyethyl)-5-(4-methylphenyl)-8-oxo-1,7-naphthyridine-6-carboxamide
CAS No.:183550-71-2
Molecular Formula:C₂₇H₂₁F₆N₃O₃
Molecular Weight:549.472
Hs Code.:

Synonyms:N-[3,5-bis(trifluoromethyl)benzyl]-7,8-dihydro-7-(2-hydroxyethyl)-5-(4-methylphenyl)-8-oxo-1,7-naphthyridine-6-carboxamide

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Chemical Property of N-[3,5-bis(trifluoromethyl)benzyl]-7,8-dihydro-7-(2-hydroxyethyl)-5-(4-methylphenyl)-8-oxo-1,7-naphthyridine-6-carboxamide

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Technology Process of N-[3,5-bis(trifluoromethyl)benzyl]-7,8-dihydro-7-(2-hydroxyethyl)-5-(4-methylphenyl)-8-oxo-1,7-naphthyridine-6-carboxamide

There total 8 articles about N-[3,5-bis(trifluoromethyl)benzyl]-7,8-dihydro-7-(2-hydroxyethyl)-5-(4-methylphenyl)-8-oxo-1,7-naphthyridine-6-carboxamide 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: 70.0%

: 141-43-5
ethanolamine

: 183550-80-3
N-[3,5-bis(trifluoromethyl)benzyl]-5-(4-methylphenyl)-8-oxo-8H-pyrano[3,4-b]pyridine-6-carboxamide

: 183550-71-2
N-[3,5-bis(trifluoromethyl)benzyl]-7,8-dihydro-7-(2-hydroxyethyl)-5-(4-methylphenyl)-8-oxo-1,7-naphthyridine-6-carboxamide

Guidance literature:: ethanolamine; N-[3,5-bis(trifluoromethyl)benzyl]-5-(4-methylphenyl)-8-oxo-8H-pyrano[3,4-b]pyridine-6-carboxamide; In tetrahydrofuran; methanol; at 20 ℃;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; acetonitrile; for 1h; Heating;
DOI:10.1021/jm990220r

Reference yield:

: 116060-91-4
3-(4-methylbenzoyl)-2-pyridine carboxylic acid

: 183550-71-2
N-[3,5-bis(trifluoromethyl)benzyl]-7,8-dihydro-7-(2-hydroxyethyl)-5-(4-methylphenyl)-8-oxo-1,7-naphthyridine-6-carboxamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: thionyl chloride, DMF / tetrahydrofuran / 2 h / Heating

2.1: NaH / tetrahydrofuran / 0.5 h / -10 °C

3.1: 85 percent / AcOH, conc. HCl / 3 h / Heating

4.1: thionyl chloride, DMF / 1,2-dichloro-ethane; tetrahydrofuran / 1.5 h / Heating

5.1: Et₃N / tetrahydrofuran / 0.5 h / 20 °C

6.1: tetrahydrofuran; methanol / 20 °C

6.2: 70 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile; toluene / 1 h / Heating

With hydrogenchloride; thionyl chloride; sodium hydride; acetic acid; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; 1,2-dichloro-ethane; 1.1: Chlorination / 2.1: cyclocondensation / 3.1: Decarboxylation / 4.1: Chlorination / 5.1: amidation / 6.1: Condensation / 6.2: Dehydration;
DOI:10.1021/jm990220r

Reference yield:

: 508210-05-7
3-p-toluoyl-pyridine-2-carbonyl chloride

: 183550-71-2
N-[3,5-bis(trifluoromethyl)benzyl]-7,8-dihydro-7-(2-hydroxyethyl)-5-(4-methylphenyl)-8-oxo-1,7-naphthyridine-6-carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / tetrahydrofuran / 0.5 h / -10 °C

2.1: 85 percent / AcOH, conc. HCl / 3 h / Heating

3.1: thionyl chloride, DMF / 1,2-dichloro-ethane; tetrahydrofuran / 1.5 h / Heating

4.1: Et₃N / tetrahydrofuran / 0.5 h / 20 °C

5.1: tetrahydrofuran; methanol / 20 °C

5.2: 70 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile; toluene / 1 h / Heating

With hydrogenchloride; thionyl chloride; sodium hydride; acetic acid; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; 1,2-dichloro-ethane; 1.1: cyclocondensation / 2.1: Decarboxylation / 3.1: Chlorination / 4.1: amidation / 5.1: Condensation / 5.2: Dehydration;
DOI:10.1021/jm990220r