benzyl 3-(2-methoxy-2-oxoacetyl)-2-methyl-4-(p-tolyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Base Information

Chemical Name:benzyl 3-(2-methoxy-2-oxoacetyl)-2-methyl-4-(p-tolyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate
CAS No.:1449609-67-9
Molecular Formula:C₂₇H₂₆N₂O₅
Molecular Weight:458.514
Hs Code.:

Synonyms:benzyl 3-(2-methoxy-2-oxoacetyl)-2-methyl-4-(p-tolyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

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Chemical Property of benzyl 3-(2-methoxy-2-oxoacetyl)-2-methyl-4-(p-tolyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

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Technology Process of benzyl 3-(2-methoxy-2-oxoacetyl)-2-methyl-4-(p-tolyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

There total 9 articles about benzyl 3-(2-methoxy-2-oxoacetyl)-2-methyl-4-(p-tolyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate 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: 32.0%

: 1-(cyanomethyl)tetrahydro-1H-thiophen-1-ium bromide salt

: 67-56-1
methanol

: 1449609-64-6
methyl 2-(6-([1,1'-biphenyl]-4-yl)-4-(4-fluorophenyl)-2-isopropyl-8,8-dimethyl-5,6,7,8-tetrahydro-1,6-naphthyridin-3-yl)-2-(tert-butoxy)acetate

: 1449609-67-9
benzyl 3-(2-methoxy-2-oxoacetyl)-2-methyl-4-(p-tolyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Guidance literature:: methyl 2-(6-([1,1'-biphenyl]-4-yl)-4-(4-fluorophenyl)-2-isopropyl-8,8-dimethyl-5,6,7,8-tetrahydro-1,6-naphthyridin-3-yl)-2-(tert-butoxy)acetate; With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 1h;

1-(cyanomethyl)tetrahydro-1H-thiophen-1-ium bromide salt; With triethylamine; In dichloromethane; at 20 ℃; for 20h;

methanol; With Oxone; In water; at 20 ℃; for 2h;

Reference yield:

: 1449611-40-8
C₂₆H₂₉NO₆

: 1449609-67-9
benzyl 3-(2-methoxy-2-oxoacetyl)-2-methyl-4-(p-tolyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: ammonium acetate / Heating; Acidic conditions

2: ammonium cerium (IV) nitrate; trifluoroacetic acid / 1.5 h

3: lithium chloride; 2,6-dimethylpyridine / dimethyl sulfoxide / 2 h / 130 °C

4: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 1 h

5: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 h

6: oxone / water / 2 h

With 2,6-dimethylpyridine; ammonium cerium (IV) nitrate; oxone; oxalyl dichloride; ammonium acetate; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; trifluoroacetic acid; lithium chloride; In dichloromethane; water; dimethyl sulfoxide;
DOI:10.1021/acs.jmedchem.8b01473

Reference yield:

: 1449609-65-7
6-benzyl 3-methyl 2-methyl-4-(p-tolyl)-7,8-dihydro-1,6-naphthyridine-3,6(5H)-dicarboxylate

: 1449609-67-9
benzyl 3-(2-methoxy-2-oxoacetyl)-2-methyl-4-(p-tolyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: lithium chloride; 2,6-dimethylpyridine / dimethyl sulfoxide / 2 h / 130 °C

2: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 1 h

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 h

4: oxone / water / 2 h

With 2,6-dimethylpyridine; oxone; oxalyl dichloride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; lithium chloride; In dichloromethane; water; dimethyl sulfoxide;
DOI:10.1021/acs.jmedchem.8b01473