7-[(R)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-butyl]-8-oxo-5-p-tolyl-7,8-dihydro-[1,7]naphthyridine-6-carboxylic acid 3,5-bis-trifluoromethyl-benzylamide

Base Information

• Chemical Name: 7-[(R)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-butyl]-8-oxo-5-p-tolyl-7,8-dihydro-[1,7]naphthyridine-6-carboxylic acid 3,5-bis-trifluoromethyl-benzylamide
• CAS No.: 217099-10-0
• Molecular Formula: C₃₅H₃₅F₆N₃O₄
• Molecular Weight: 675.671
• Mol file: 217099-10-0.mol

Synonyms:7-[(R)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-butyl]-8-oxo-5-p-tolyl-7,8-dihydro-[1,7]naphthyridine-6-carboxylic acid 3,5-bis-trifluoromethyl-benzylamide

Chemical Property of 7-[(R)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-butyl]-8-oxo-5-p-tolyl-7,8-dihydro-[1,7]naphthyridine-6-carboxylic acid 3,5-bis-trifluoromethyl-benzylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-[(R)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-butyl]-8-oxo-5-p-tolyl-7,8-dihydro-[1,7]naphthyridine-6-carboxylic acid 3,5-bis-trifluoromethyl-benzylamide

There total 7 articles about 7-[(R)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-butyl]-8-oxo-5-p-tolyl-7,8-dihydro-[1,7]naphthyridine-6-carboxylic acid 3,5-bis-trifluoromethyl-benzylamide 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:

N-[3,5-bis(trifluoromethyl)benzyl]-5-(4-methylphenyl)-8-oxo-8H-pyrano[3,4-b]pyridine-6-carboxamide (183550-80-3) + (R)-4-amino-2-methyl-1-butanol tetrahydropyranyl ether (183551-55-5) → 7-[(R)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-butyl]-8-oxo-5-p-tolyl-7,8-dihydro-[1,7]naphthyridine-6-carboxylic acid 3,5-bis-trifluoromethyl-benzylamide (217099-10-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; Multistep reaction; 1.) THF, MeOH, r.t., 16 h, 2.) toluene, MeCN, reflux, 1h;

DOI:10.1039/a805333b

Reference yield:

5-(4-methylphenyl)-8-oxo-8H-pyrano[3,4-b]pyridine-6-carboxylic acid (183550-78-9) → 7-[(R)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-butyl]-8-oxo-5-p-tolyl-7,8-dihydro-[1,7]naphthyridine-6-carboxylic acid 3,5-bis-trifluoromethyl-benzylamide (217099-10-0)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3.1: tetrahydrofuran; methanol / 16 h / 20 °C

3.2: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile; toluene / 1 h / Heating

With thionyl chloride; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; 1,2-dichloro-ethane; 1.1: Chlorination / 2.1: amidation / 3.1: Condensation / 3.2: Dehydration;

DOI:10.1021/jm990220r

Reference yield:

3-(4-methylbenzoyl)-2-pyridine carboxylic acid (116060-91-4) → 7-[(R)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-butyl]-8-oxo-5-p-tolyl-7,8-dihydro-[1,7]naphthyridine-6-carboxylic acid 3,5-bis-trifluoromethyl-benzylamide (217099-10-0)

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 / 16 h / 20 °C

6.2: 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

upstream raw materials:

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

(R)-4-amino-2-methyl-1-butanol tetrahydropyranyl ether

3-(4-methylbenzoyl)-2-pyridine carboxylic acid

3-p-toluoyl-pyridine-2-carbonyl chloride

Downstream raw materials:

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

(aR,9R)-7-[3,5-bis(trifluoromethyl)benzyl]-8,9,10,11-tetrahydro-9-methyl-5-(4-methylphenyl)-7H-[1,4]diazocino[2,1-g][1,7]naphthyridine-6,13-dione

(aS,9R)-7-[3,5-bis(trifluoromethyl)benzyl]-8,9,10,11-tetrahydro-9-methyl-5-(4-methylphenyl)-7H-[1,4]diazocino[2,1-g][1,7]naphthyridine-6,13-dione