2-tert-butoxycarbonylamino-8-(4'-nitro-biphenyl-4-ylmethyl)-5,8-dihydro-6H-[1,7]naphthyridine-7-carboxylic acid ethyl ester

Base Information

• Chemical Name: 2-tert-butoxycarbonylamino-8-(4'-nitro-biphenyl-4-ylmethyl)-5,8-dihydro-6H-[1,7]naphthyridine-7-carboxylic acid ethyl ester
• CAS No.: 316155-99-4
• Molecular Formula: C₂₉H₃₂N₄O₆
• Molecular Weight: 532.596

Synonyms:2-tert-butoxycarbonylamino-8-(4'-nitro-biphenyl-4-ylmethyl)-5,8-dihydro-6H-[1,7]naphthyridine-7-carboxylic acid ethyl ester

Chemical Property of 2-tert-butoxycarbonylamino-8-(4'-nitro-biphenyl-4-ylmethyl)-5,8-dihydro-6H-[1,7]naphthyridine-7-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of 2-tert-butoxycarbonylamino-8-(4'-nitro-biphenyl-4-ylmethyl)-5,8-dihydro-6H-[1,7]naphthyridine-7-carboxylic acid ethyl ester

There total 8 articles about 2-tert-butoxycarbonylamino-8-(4'-nitro-biphenyl-4-ylmethyl)-5,8-dihydro-6H-[1,7]naphthyridine-7-carboxylic acid ethyl 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:

3-amino-pyridine-4-carbaldehyde (55279-29-3) → 2-tert-butoxycarbonylamino-8-(4'-nitro-biphenyl-4-ylmethyl)-5,8-dihydro-6H-[1,7]naphthyridine-7-carboxylic acid ethyl ester (316155-99-4)

Guidance literature:

Multi-step reaction with 6 steps

1: NaOH / H₂O

2: 51 percent / DPPA / Heating

3: 61 percent / CH₂Cl₂ / 72 h / 0 - 20 °C

4: 95 percent / NH₄CO₂H / Pd/C / methanol

5: pyridine

6: Cs₂CO₃ / PdCl₂*dppf / tetrahydrofuran

With pyridine; sodium hydroxide; diphenyl-phosphinic acid; ammonium formate; caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; 1: Condensation / 2: Esterification / 3: Alkylation / 4: Hydrogenation / 5: Esterification / 6: Arylation;

DOI:10.1016/S0040-4039(00)01400-3

Reference yield:

3--4-pyridinecarboxaldehyde (116026-95-0) → 2-tert-butoxycarbonylamino-8-(4'-nitro-biphenyl-4-ylmethyl)-5,8-dihydro-6H-[1,7]naphthyridine-7-carboxylic acid ethyl ester (316155-99-4)

Guidance literature:

Multi-step reaction with 7 steps

1: TFA / CH₂Cl₂

2: NaOH / H₂O

3: 51 percent / DPPA / Heating

4: 61 percent / CH₂Cl₂ / 72 h / 0 - 20 °C

5: 95 percent / NH₄CO₂H / Pd/C / methanol

6: pyridine

7: Cs₂CO₃ / PdCl₂*dppf / tetrahydrofuran

With pyridine; sodium hydroxide; diphenyl-phosphinic acid; ammonium formate; caesium carbonate; trifluoroacetic acid; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; 1: Decarboxylation / 2: Condensation / 3: Esterification / 4: Alkylation / 5: Hydrogenation / 6: Esterification / 7: Arylation;

DOI:10.1016/S0040-4039(00)01400-3

Reference yield:

2-carboxy-(1,6)-naphthyridine (316155-87-0) → 2-tert-butoxycarbonylamino-8-(4'-nitro-biphenyl-4-ylmethyl)-5,8-dihydro-6H-[1,7]naphthyridine-7-carboxylic acid ethyl ester (316155-99-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 51 percent / DPPA / Heating

2: 61 percent / CH₂Cl₂ / 72 h / 0 - 20 °C

3: 95 percent / NH₄CO₂H / Pd/C / methanol

4: pyridine

5: Cs₂CO₃ / PdCl₂*dppf / tetrahydrofuran

With pyridine; diphenyl-phosphinic acid; ammonium formate; caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 1: Esterification / 2: Alkylation / 3: Hydrogenation / 4: Esterification / 5: Arylation;

DOI:10.1016/S0040-4039(00)01400-3

upstream raw materials:

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene

3-amino-pyridine-4-carbaldehyde

3--4-pyridinecarboxaldehyde

2-carboxy-(1,6)-naphthyridine

Downstream raw materials:

8-(4'-amino-biphenyl-4-ylmethyl)-5,6,7,8-tetrahydro-[1,7]naphthyridin-2-ylamine

2-amino-8-(4'-amino-biphenyl-4-ylmethyl)-5,8-dihydro-6H-[1,7]naphthyridine-7-carboxylic acid tert-butyl ester

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