4-{4-[2-(3,5-di-tert-butyl-phenyl)-ethoxy]-phenyl}-N²-(4-methoxy-benzyl)-[1,8]naphthyridine-2,7-diamine

Base Information

• Chemical Name: 4-{4-[2-(3,5-di-tert-butyl-phenyl)-ethoxy]-phenyl}-N²-(4-methoxy-benzyl)-[1,8]naphthyridine-2,7-diamine
• CAS No.: 858859-71-9
• Molecular Formula: C₃₈H₄₄N₄O₂
• Molecular Weight: 588.793

Synonyms:4-{4-[2-(3,5-di-tert-butyl-phenyl)-ethoxy]-phenyl}-N²-(4-methoxy-benzyl)-[1,8]naphthyridine-2,7-diamine

Chemical Property of 4-{4-[2-(3,5-di-tert-butyl-phenyl)-ethoxy]-phenyl}-N²-(4-methoxy-benzyl)-[1,8]naphthyridine-2,7-diamine

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Technology Process of 4-{4-[2-(3,5-di-tert-butyl-phenyl)-ethoxy]-phenyl}-N²-(4-methoxy-benzyl)-[1,8]naphthyridine-2,7-diamine

There total 10 articles about 4-{4-[2-(3,5-di-tert-butyl-phenyl)-ethoxy]-phenyl}-N²-(4-methoxy-benzyl)-[1,8]naphthyridine-2,7-diamine 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:

3,5-di-tert-butylbenzyl bromide (62938-08-3) → 4-{4-[2-(3,5-di-tert-butyl-phenyl)-ethoxy]-phenyl}-N2-(4-methoxy-benzyl)-[1,8]naphthyridine-2,7-diamine (858859-71-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 60 percent / dimethylsulfoxide / 20 h / 20 °C

2.1: 88 percent / aq. KOH / tetrahydrofuran; ethanol / 192 h / 100 °C

3.1: 92 percent / LiAlH₄ / ethanol / 3 h / Heating

4.1: 95 percent / pyridine / 18 h / 0 °C

5.1: BBr₃ / CH₂Cl₂ / 0 - 20 °C

5.2: K₂CO₃ / dimethylformamide / 12 h / 70 °C

5.3: 550 mg / pyridine / 48 h / 100 °C

With pyridine; potassium hydroxide; lithium aluminium tetrahydride; boron tribromide; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/ol050987f

Reference yield:

N-[7-chloro-5-(4-methoxy-phenyl)-[1,8]naphthyridin-2-yl]-acetamide (858859-63-9) + toluene-4-sulfonic acid 2-(3,5-di-tert-butyl-phenyl)-ethyl ester (858859-68-4) + 4-methoxy-benzylamine (2393-23-9) → 4-{4-[2-(3,5-di-tert-butyl-phenyl)-ethoxy]-phenyl}-N2-(4-methoxy-benzyl)-[1,8]naphthyridine-2,7-diamine (858859-71-9)

Guidance literature:

N-[7-chloro-5-(4-methoxy-phenyl)-[1,8]naphthyridin-2-yl]-acetamide; With boron tribromide; In dichloromethane; at 0 - 20 ℃;

toluene-4-sulfonic acid 2-(3,5-di-tert-butyl-phenyl)-ethyl ester; With potassium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 12h;

4-methoxy-benzylamine; With pyridine; at 100 ℃; for 48h;

DOI:10.1021/ol050987f

Reference yield:

2-(3,5-di-tert-butylphenyl)ethanol (858859-67-3) → 4-{4-[2-(3,5-di-tert-butyl-phenyl)-ethoxy]-phenyl}-N2-(4-methoxy-benzyl)-[1,8]naphthyridine-2,7-diamine (858859-71-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / pyridine / 18 h / 0 °C

2.1: BBr₃ / CH₂Cl₂ / 0 - 20 °C

2.2: K₂CO₃ / dimethylformamide / 12 h / 70 °C

2.3: 550 mg / pyridine / 48 h / 100 °C

With pyridine; boron tribromide; In dichloromethane;

DOI:10.1021/ol050987f

upstream raw materials:

N-[7-chloro-5-(4-methoxy-phenyl)-[1,8]naphthyridin-2-yl]-acetamide

toluene-4-sulfonic acid 2-(3,5-di-tert-butyl-phenyl)-ethyl ester

4-methoxy-benzylamine

2-(3,5-di-tert-butylphenyl)ethanol

Downstream raw materials:

1-butyl-3-[5-{4-[2-(3,5-di-tert-butyl-phenyl)-ethoxy]-phenyl}-7-(4-methoxy-benzylamino)-[1,8]naphthyridin-2-yl]-urea

1-(7-amino-5-{4-[2-(3,5-di-tert-butyl-phenyl)-ethoxy]-phenyl}-[1,8]naphthyridin-2-yl)-3-butyl-urea

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